Category: 6797-13-3

Feng, Feng; Ye, Jia; Cheng, Zheng; Xu, Xiaoliang; Zhang, Qunfeng; Ma, Lei; Lu, Chunshan; Li, Xiaonian published an article about the compound: 2-Ethylbenzo[d]oxazole( cas:6797-13-3,SMILESS:CCC1=NC2=CC=CC=C2O1 ).Name: 2-Ethylbenzo[d]oxazole. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:6797-13-3) through the article.

The coupling of multi-step reactions catalyzed by a heterogeneous catalyst is an important path to accomplish some unconventional chem. transformations. Since the starting materials generated from previous steps were adsorbed on the catalyst, the activation energy of following steps was largely decreased, and thus the reaction conditions were more mild and environmentally friendly. Catalyzed by a multifunctional Cu-Pd/γ-Al2O3 catalyst, the transfer hydrogenation and successive cyclization coupling reaction from o-nitroaniline and alc. to afford benzimidazole derivatives I (R1 = H, CH3, OCH3, Cl, F; R2 = H, CH3, C2H5, n-Pr, Ph) in high yield was realized. The catalyst could be reused several times without loss of activity. The synergies of reforming hydrogenation of Cu-Pd bimetal and support acidity of γ-Al2O3 were responsible for this catalytic transformation.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Catalytic Direct Cyanomethylenation of C(sp3)-H Bonds via A One-Step Double C-C Bond Formation, published in , which mentions a compound: 6797-13-3, mainly applied to benzoxazolyl arylacrylonitrile diastereoselective preparation; arylmethyl benzoxazole DMF trimethylsilyl cyanide cyanomethylenation catalyst palladium copper; benzothiazolyl arylacrylonitrile diastereoselective preparation; benzothiazole arylmethyl DMF trimethylsilyl cyanide cyanomethylenation catalyst palladium copper; oxo aryl arylbutenenitrile diastereoselective preparation; aryl arylethanone DMF trimethylsilyl cyanide cyanomethylenation catalyst palladium copper, Application In Synthesis of 2-Ethylbenzo[d]oxazole.

An elegant and catalytic procedure for the one-step cyanomethylenation of C(sp3)-H bonds adjacent to benzazoles and ketones was described herein using DMF as a C-1 unit and TMSCN as the cyanide source. The copper mediated reaction between DMF and TMSCN gave a cyanomethylene radical intermediate that reacts with 2-alkylbenzazoles or alkylketones to furnish desired cyanomethylenated compounds I [R = Me, Ph, 4-MeOC6H4, etc.; R3 = H, 5-Cl, 6-Me, etc.; X = O, S] and II [R1 = Ph, 4-MeOC6H4, 4-BrC6H4 etc.; R2 = Ph, 4-BrC6H4, 4-O2NC6H4] under palladium catalysis. Subsequent interconversion of cyanomethylenated products I and II has made the protocol synthetically attractive.

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SDS of cas: 6797-13-3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Graphene oxide as a heterogeneous reagent promoted synthesis of 2-substituted 1,3-benzazoles in water. Author is Khalili, Dariush; Banazadeh, Ali Reza.

An efficient chem. method for the synthesis of benzimidazoles, benzothiazoles, and benzoxazoles has been developed through the condensation of various aldehydes with o-phenylenediamine, o-aminothiophenol, and o-aminophenol using graphene oxide (GO) as an oxidant in water. These benzazoles are also prepared through a one-pot oxidation/condensation tandem process by reacting alcs. with 2-amino-(thio)phenol/aniline in the presence of GO in poly(ethylene glycol) as a safe media. Moreover, this carbonaceous material could be readily separated using a simple filtration.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 6797-13-3, is researched, SMILESS is CCC1=NC2=CC=CC=C2O1, Molecular C9H9NOJournal, Article, Combinatorial Chemistry & High Throughput Screening called A Green and Efficient Protocol for the Synthesis of Quinoxaline, Benzoxazole and Benzimidazole Derivatives Using Heteropolyanion-Based Ionic Liquids: As a Recyclable Solid Catalyst, Author is Vahdat, Seyed Mohammad; Baghery, Saeed, the main research direction is ionic liquid preparation green chem benzimidazole benzoxazole.Product Details of 6797-13-3.

In this paper, the authors introduce two non-conventional ionic liquid compounds which are composed of propane sulfonate functionalized organic cations and heteropoly anions as green solid acid catalysts for the highly efficient and green synthesis of 2,3-disubstituted quinoxaline derivatives These ionic liquids are in the solid state at room temperature and the synthesis is carried out by a one-pot condensation reaction of various phenylenediamine derivatives with 1,2-diketone derivatives Benzoxazole and benzimidazole derivatives were also synthesized by these novel catalysts by a one-pot condensation from reaction orthoester with o-aminophenol (synthesis of benzoxazole derivatives) and phenylenediamine (synthesis of benzimidazole derivatives). All experiments successfully resulted in the desired products. The described novel synthesis method has several advantages of easy handling of reactants, mild reaction conditions, high yields, short reaction times, simplicity and easy workup compared to the traditional method of synthesis. The synthesis of the target compounds was achieved using as catalysts 1-methyl-3-(3-sulfopropyl)-1H-imidazolium tetracosa-μ-oxododecaoxo[μ12-[phosphato(3-)-κO:κO:κO:κO’:κO’:κO’:κO”:κO”:κO”:κO”’:κO”’:κO”’]]dodecatungstate(3-) (3:1) [1-methyl-3-(3-sulfopropyl)-1H-imidazolium tungstophosphate [PW12O403-]] and N,N,N-triethyl-3-sulfo-1-propanaminium tetracosa-μ-oxododecaoxo[μ12-[phosphato(3-)-κO:κO:κO:κO’:κO’:κO’:κO”:κO”:κO”:κO”’:κO”’:κO”’]]dodecatungstate(3-) (3:1) [1-methyl-3-sulfo-1-propanaminium tungstophosphate [PW12O403-]] as catalysts. The title compounds thus formed included 2,3-diphenylquinoxaline derivatives, 1H-benzimidazole derivatives, benzoxazole derivatives, dibenzo[a,c]phenazine, acenaphtho[1,2-b]quinoxaline, 2,5-dimethylbenzoxazole.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Expeditious and efficient synthesis of benzoxazoles, benzothiazoles, benzimidazoles catalyzed by Ga(OTf)3 under solvent-free conditions, published in 2011-08-31, which mentions a compound: 6797-13-3, Name is 2-Ethylbenzo[d]oxazole, Molecular C9H9NO, Computed Properties of C9H9NO.

A new and efficient method for the synthesis of benzoxazoles, benzothiazoles, benzimidazoles by cyclocondensation of o-substituted aminoaroms. with ortho esters in the presence of catalytic amounts of Ga(OTf)3 under solvent-free conditions is presented. The remarkable features of this new protocol are high conversion, very short reaction times, cleaner reaction profiles under solvent-free conditions, straightforward procedure, and use of a relatively non-toxic catalyst.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques called Dipole moments and electron distribution of some benzazole heterocycles, Author is Galy, Anne Marie; Llinares, Jeannine; Galy, Jean Pierre; Barbe, Jacques, which mentions a compound: 6797-13-3, SMILESS is CCC1=NC2=CC=CC=C2O1, Molecular C9H9NO, Formula: C9H9NO.

The dipole moments of 2-substituted benzoxazoles (I; X = O, R = H, Me, Et, MeS, NH2, NHEt, CN, Ph), benzothiazoles (I; X = S, R = Me, MeS, MeO, NH2, Me2N, CN) and II (Z = O, R1 = H, Me; Z = S, R1 = Me) were measured in C6H6 and compared with values calculated by a vectorial mol. increment method. The results indicate a slight delocalization of the C(2)-N(3) double bond. Benzoxazolone is in tautomeric equilibrium

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COA of Formula: C9H9NO. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Addition of 2-ethylbenzazoles to aromatic aldehydes in the presence of aqueous sodium hydroxide. Author is Dryanska, V.; Ivanov, K.; Nikolov, M..

Treating benzazoles I with R1CHO (R1 = Ph, 2-ClC6H4, 4-ClC6H4, 2-MeC6H4, 4-MeC6H4, 4-MeOC6H4) gave II and III, whereas R1CHO (R1 = 2-BrC6H4, 2,4-(MeO)2C6H3, 1-naphthyl, 4-Me2NC6H4) gave only III. IV were similarly obtained from 2-benzylbenzoxazole.

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Synthetic Route of C9H9NO. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Ag@TiO2 nanocomposite; synthesis, characterization and its application as a novel and recyclable catalyst for the one-pot synthesis of benzoxazole derivatives in aqueous media. Author is Maleki, Behrooz; Baghayeri, Mehdi; Vahdat, Seyed Mohammad; Mohammadzadeh, Abbas; Akhoondi, Somaieh.

A series of benzoxazole derivatives I (R = H, 3-NO2C6H4, CH2CH3, 3-CH3OC6H4, etc.) were synthesized via Ag@TiO2 nanocomposite catalyzed one-pot condensation of 2-aminophenol and several aromatic aldehydes or orthoesters or carboxylic acids or amides or acyl chlorides in water at room temperature with excellent yields. The short reaction times, high yields, safety and mild conditions, simplicity, non-toxicity and easy workup were the main merits of this protocol.

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Saha, Prasenjit; Ramana, Tamminana; Purkait, Nibadita; Ali, Ashif Md; Paul, Rajesh; Punniyamurthy, Tharmalingam published the article 《Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles》. Keywords: benzimidazole aminobenzimidazole aminobenzothiazole benzoxazole preparation; intramol cyclization bromoaryl derivative copper oxide nanoparticle catalyst.They researched the compound: 2-Ethylbenzo[d]oxazole( cas:6797-13-3 ).Product Details of 6797-13-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:6797-13-3) here.

The synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles is described via intramol. cyclization of o-bromoaryl derivatives using copper(II) oxide nanoparticles in DMSO under air. E.g., cyclization of o-bromoaryl amidine I gave 95% benzimidazoles II. The procedure is exptl. simple, general, efficient, and free from addition of external chelating ligands. It is a heterogeneous process and the copper(II) oxide nanoparticles can be recovered and recycled without loss of activity.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Chain-substituted methinecyanines and styryl dyes, published in 1956, which mentions a compound: 6797-13-3, mainly applied to , Formula: C9H9NO.

Various methinecyanines carrying a substituent on the chain have been prepared and their absorption maximum compared with those of the parent dyes. The procedure of Schott [Ber. 29, 1985(1896)] in which PhCH2CO2H (I) and PCl5 were reported to give PhCH2COCl (II) could not be reproduced. Instead, to 18 cc. boiling SOCl2 was added in 10 min. 27.2 g. I, the whole refluxed 0.5 hr. and distilled to give 77% II, b17 96-8°. To 17.8 g. II and 1 equivalent o-HSC6H4NH2.HCl was added 0.33 mole P2O5, the whole heated 8 min. in an oil bath at 160-175°, warmed with aqueous NaOH, the whole cooled, extracted with Et2O, and the Et2O extracts concentrated and distilled to give 29% 2-benzylbenzothiazole (III), b0.5 157-63°. III (9.82 g.) and 1.2 equivalents EtI heated 48 hrs. at 100° and the mixture treated with Me2CO gave 57% of the ethiodide (IV), yellow crystals, m. 181° (from EtOH). In similar fashion, were prepared 73% 2-(p-nitrobenzyl)benzothiazole, m. 115° (from EtOH) [ethiodide (V), m. 249° (decomposition)(from MeOH)] and 18% 2-(chloromethyl)benzothiazole (VA), b0.2 79-91°, m. 34° (from petr. ether); VA and EtI gave no ethiodide. To 20.85 g. Zn salt of o-H2NC6H4SH in 90 cc. boiling dry C6H6 was added gradually 1 equivalent EtO2CCOCl (VI) (b21 75-8°) in 120 cc. dry C6H6, the whole refluxed 6 hrs., filtered, the insoluble residue extracted with boiling C6H6, the C6H6 filtrates and extracts combined, washed with excess aqueous NaHCO3, washed with H2O, dried, and distilled to give 2-ethoxycarbonylmethylbenzothiazole (VIA), yellow liquid, b0.5 121-26° [methiodide (VII), m. 175° (decomposition) (from MeOH-Me2CO); ethiodide (VIII), m. 190° (decomposition) (from EtOH)]. To 0.81 g. o-HSC6H4NHEt (IX) in 4 cc. dry C6H6 was added 1.1 equivalent VI in 2 cc. dry C6H6, the whole cooled to room temperature, the liquid decanted, the gum washed with C6H6, the C6H6-insoluble residue dissolved in 2 cc. MeOH, and the MeOH solution treated with a warm solution of 2 equivalent KI in 4 cc. H2O to give VIII. By the same procedure, IX and ClCH2COCl in C6H6, followed by KI gave 13-19% 2-(o-ethylaminophenylthiomethyl)benzothiazole ethiodide (IXA), m. 158° (decomposition) (from MeOH). 2-Ethylthiobenzothiazole (X) 19.93 g. and 1 equivalent neutral Et2SO4 heated 8 hrs. at 110-20°, the whole dissolved in 120 cc. H2O, the solution extracted with Et2O, the aqueous solution separated, cooled, and treated with an excess of NaOH gave 30-83% 3-ethyl-2-oxobenzothiazoline (XI), colorless liquid, b0.5 101° (a contaminant which was difficult to sep. from XI was 3-ethyl-2-thiobenzothiazoline (XII)). X (19.5 g.) and 1 equivalent Et2SO4 heated 8 hrs. at 110-20°, the whole dissolved in 100 cc. C5H5N, and the solution refluxed 1 hr. and poured into warm H2O gave 82% XII, m. 77-8° (from MeOH). Freshly prepared 2-ethylthiobenzothiazole.EtI (XIII) 0.63 g. and 3 cc. C5H5N refluxed 10 min. and the whole poured into 12 cc. H2O gave 68% XII. On standing for several months, XIII was gradually converted to XII. Distilled XI (12.1 g.) in 24 cc. EtOH and 6 equivalents KOH in 70 cc. EtOH refluxed 1 hr., cooled, the K2CO3 filtered, the filtrate evaporated to dryness, the residue dissolved in 100 cc. H2O, the H2O solution cooled and made acidic with concentrated HCl, the oily product extracted with C6H6, and the C6H6 solution dried, concentrated, and distilled gave 77% IX, b0.5 57-60°. XII (19.53 g.) in 40 cc. EtOH and 6 equivalents KOH in 105 cc. EtOH refluxed 6 hrs. and treated as above gave 70% IX. o-H2NC6H4OH (XIV) 42.6 g. was added slowly to 3 equivalents (EtCO)2O, the whole was heated 0.5 hr. on a H2O bath, then distilled from an oil bath, rejecting material b. below 150°. The residual material was washed thoroughly with 10% Na2CO3 solution, separated, and distilled to give 28% 2-ethylbenzoxazole (XIVA), b0.3-0.5 40-3°; ethiodide (XV), colorless crystals, m. 198° (decomposition) (from EtOH). XIV (10.9 g.) and 1 equivalent PhCH2CO2H heated 3 hrs. at 200-25° (H2O vapor allowed to distil), the mixture cooled, treated with aqueous NaOH, extracted with C6H6, and the C6H6 solution concentrated and distilled gave 48% 2-benzylbenzoxazole (XVA), b0.3 118-25°; no ethiodide could be prepared and the Et p-toluene-sulfonate (XVI) was a gum which could be dissolved in EtOH and used in the dye condensations described below. To 1 mole 2-ethylbenzothiazole-EtI (XVII) and 1 mole 2-iodoquinoline-EtI (XVIII) in EtOH there was added 2.1 moles Et3N. The mixture stirred and refluxed 1-30 min., the whole cooled, treated with Et2O, the precipitated gum separated, and washed with Et2O gave 54-84% [2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)]methylmethinecyanine iodide (XIX), olive-green dye, softens 125°, m. about 148° (from Me2CO and from EtOH). XIX was homogeneous as shown by a chromatogram from CHCl3 on alumina. XIX had a slight desensitizing action toward a photographic emulsion. In a similar experiment with 2-ethylbenzothiazole-p-MeC6H4SO3Et (XIXA), the gum precipitated with Et2O and heated with aqueous KI gave 66% XIX. XVII (0.8 g.) and 2-ethylthioquinoline reacted as above gave a mixture of 12% XIX and a trace of [2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)]methinecyanine iodide, separated by absorption on alumina and elution with CHCl3-EtOH. In a similar fashion, XVII and XIII gave 8% bis[2-(3-ethylbenzothiazole)]methylmethinecyanine iodide, brick-red crystals, m. about 214° and a trace of the bis[2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)]phenylmethinecyanine iodide (from EtOH); 2-methylbenzothiazole-EtI and 2-iodo-5,6-benzoquinoline-EtI (XX) gave 42% [2-(1-ethyl-5,6-benzoquinoline)][2-(3-ethylbenzothiazole)]methinecyanine iodide, red-orange crystals, m. 258° (decomposition) (from MeOH); XVII and XX gave 67% [2-(1-ethyl-5,6-benzoquinoline)][2-(3-ethylbenzothiazole)]methylmethinecyanine iodide, dark-purple crystals, m. about 225° (violent decomposition) (from EtOH); XIII and XX gave 42% [2-(1-ethyl-5,6-benzoquinoline)][2-(3-ethylbenzothiazole)]phenylmethinecyanine iodide, purple crystals, m. about 175° (decomposition) (from EtOH); XVII and 1-iodoisoquinoline-EtI (XXI) gave the dye iodide, which in hot EtOH with hot aqueous NaClO4 gave 72% [2-(3-ethylbenzothiazole)][1-(2-ethylisoquinoline)]-methylmethinecyanine perchlorate, vermillion crystals, m. about 164° (decomposition) (from EtOH); III and XXI gave 36% [2-(3-ethylbenzothiazole)][1-(2-ethylisoquinoline)]phenylmethinecyanine iodide, maroon crystals, m. 227° (decomposition) (from EtOH); and XIXA and 4-iodoquinoline.EtI (XXII) (the reaction mixture after 2-min. reflux was treated with aqueous KI) gave 49% [2-(3-ethylbenzothiazole)][4-(1-ethylquinoline)]methylmethinecyanine iodide (XXIII), olive-green crystals, m. 185° (decomposition) (from EtOH). XVII 1 mole, 3 moles quinoline-EtI, 3 moles KOH, and EtOH refluxed 0.5 hr., the solid (XXIV) filtered, the XXIV (apocyanines) boiled with 25 cc. EtOH, the solid (XXV) filtered, washed with 5 cc. hot EtOH, the combined filtrate and washings cooled gave 8% erythroapocyanine (XXVI); the XXV represented 0.5% xanthoapocyanine (XXVII) (see below); quinoline-EtI in boiling MeOH-KOH gave 31% XXIV; the XXIV extracted with boiling EtOH left 0.5% XXVII [[2-(1-ethylquinoline)][3-(1-ethylquinoline)]cyanine iodide]; the EtOH extracts were concentrated to give 14% XXVI [[3-(1-ethylquinoline)][4-(1-ethylquinoline)]cyanine iodide], m. 215-20° (decomposition) (from EtOH), λmaximum 5160 A. (ε 31,600) (in MeOH). Quinoline-EtI (7 g.) in 140 cc. EtOH and 2.76 g. Na in 20 cc. EtOH refluxed 1 hr. and the solid filtered gave 5% XXVII, orange crystals, m. >305° (from MeOH), λmaximum 4610 A., 3620 A. (ε 19,900, 6200). To IV and XXII in EtOH was added 180-mesh anhydrous K2CO3 and the whole refluxed 2 min. to give 56% [2-(3-ethylbenzothiazole)] [4-(1-ethylquinoline)] phenylmethinecyanine iodide, m. about 222° (decomposition) (from EtOH and from MeOH). V and p-MeC6H4SO3Et heated 4 hrs. at 165-75°, the product dissolved in hot EtOH, and then treated with XVIII gave the crude iodide (XXVIII) as a gum; XXVIII in CHCl3 chromatographed on alumina and eluted with CHCl3-EtOH (99:1)gave 6% [2-(3-ethylbenzothiazole)] [2-(1-ethylquinoline)]-p-nitrophenylmethinecyanine iodide, dark-purple crystals, m. 216° (decomposition) (from EtOH). 2-Ethylthioquinoline and Et2SO4 heated 8 hrs. at 110-20°, the salt in hot EtOH, VIA, and Et3N refluxed-5 min., the whole acidified with HCl, treated with NaClO4 in hot H2O, the whole cooled, the orange tar freed of liquid, washed well with hot H2O, and while wet dissolved in hot MeOH gave 66% perchlorate salt (XXIX), red crystals, m. 195° (decomposition). XXIX triturated with aqueous NaOH, the whole extracted with C6H6, the C6H6 extracts dried and concentrated, the residue dissolved in hot C6H6, the solution filtered, and the filtrate diluted with pert. ether gave 51% ethoxycarbonylmethine[2-benzothiazole] [2-(1-ethyldihydroquinoline)] (XXX), black crystals, m. 179° (decomposition), λmaximum 5170 A. (ε 13,500) (in MeOH containing NH3), λmaximum 3290 A., 4780 A. (ε 41,500, 8100) (in MeOH containing H2SO4). Similarly, X (0.98 g.) and Et2SO4 heated 8 hrs. at 110-20° and the salt (XXXI) reacted with VIA as above gave 79% perchlorate, m. 137° (decomposition) (from MeOH), which yielded 65% ethoxycarbonylmethine[2-benzothiazole][2-(3-ethyl-2,3-dihydrobenzothiazole)] (XXXII), pale-yellow crystals, m. 127° (from C6H6-petr. ether), λmaximum 3430 A. (ε 17,500) (in MeOH containing NH3), λmaximum 4230 A. (ε 9110) (in MeOH containing H2SO4). XXX and MeI heated 24 hrs. at 100°, the product washed first with hot C6H6 and then with aqueous NaHCO3, gave 25% [2-(1-ethylquinoline)] [2-(3-methyl-benzothiazole)]ethoxycarbonylmethinecyanine iodide, red crystals, m. 206° (decomposition). XXX and EtI similarly gave 32% [2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)]-ethoxycarbonylmethinecyanine iodide, orange crystals, m. 190° (decomposition) (from aqueous MeOH). XXXI, as above, and 2-methylbenzothiazole-p-MeC6H4SO3Me gave 41% [2-(3-ethylbenzothiazole)] [2-(3-methylbenzothiazole)]methinecyanine iodide, pale-yellow crystals, m. 287° (decomposition) (from EtOH). XXXII and MeI gave 25% [2-(3-ethylbenzothiazole)] [2-(3-methylbenzothiazole)]ethoxycarbonylmethinecyanine, pale-yellow crystals, m. 224° (decomposition) (from MeOH); while XXXII and EtI gave 45% [bis-2-(3-ethylbenzothiazole)]ethoxycarbonylmethinecyanine iodide, yellow crystals, m. 218° (decomposition) (from MeOH). Dibenzothiazolylmethane-EtI (XXXIIA), XVIII, Et3N, and EtOH gave 20% [2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)](2-benzothiazolyl)methinecyanine iodide, purple crystals, m. 232°. 2-Methylbenzoxazole-EtI (XXXIII) and XVIII gave 15% [2-(3-ethylbenzoxazole)][2-(1-ethylquinoline)]methinecyanine iodide, yellow crystals, m. 277° (decomposition) (from EtOH). XV and XVIII gave an unstable iodide dye, maroon crystals, m. 133° (decomposition) (from EtOH). XVI and XVIII similarly gave 26% [2-(3-ethylbenzoxazole)] [2-(1-ethylquinoline)]phenylmethinecyanine iodide, maroon crystals, m. 227° (decomposition) (from EtOH). 2-Ethylthiobenzoxazole, 2-methyl-5,6-benzoquinoline, and p-MeC6H4SO3Et heated 3.5 hrs. at 150-60°, the gum dissolved in 15 cc. hot EtOH and treated with aqueous KI gave 17% [2-(1-ethyl-5,6-benzoquinoline)] [2-(3-ethylbenzoxazole)]-methinecyanine iodide (XXXIV), m. 275° (decomposition) (from MeOH), λmaximum 4630, 4450 A. (ε 50,300, 49,400); alternatively, XX and XXXIII gave 3% XXXIV along with bis-2-(1-ethyl-5,6-benzoquinoline)methinecyanine iodide, m. 310° (decomposition). XVI and XX gave 2% [2-(1-ethyl-5,6-benzoquinoline)] [2-(3-ethylbenzoxazole)]phenylmethinecyanine iodide, red crystals, m. 183° (decomposition); XXI and 2-methylbenzoxazole-p-MeC6H4SO3Et gave 37% [2-(3-ethylbenzoxazole)][1-(2-ethylisoquinoline) ]methinecyanine iodide, red crystals, m. 228° (decomposition) (from EtOH). XVA by similar reactions (a) with XXI gave 27% of the corresponding phenylcyanine iodide, vermilion crystals, m. about 180° (decomposition) (from EtOH) and (b) with XXII 4% [2-(3-ethylbenzoxazole)] [4-(1-ethylquinoline)]phenylmethinecyanine iodide, maroon crystals, m. 224° (decomposition) (from Me2CO and from EtOH). The following compounds are derivatives of XXXV and XXXVI. 2-Methylbenzothiazole-EtI, p-Et2NC6H4CHO (XXXVII), and Ac2O were refluxed 20 min., the whole poured into a hot solution of KI in H2O, and the solid filtered and washed with Et2O to give 62% XXXV (R = H, R’ = Et) (XXXVIII), indigo-blue crystals, m. 225° (decomposition) (from MeOH). Similarly, XVII and XXXVII gave 57% XXXV (R = R’ = Me) (XXXIX), dark-blue crystals, m. 197° (decomposition) (from EtOH). The Et2O washings were evaporated, the residue dissolved in hot C6H6, and the C6H6 solution diluted with an equal volume of petr. ether to give 6% 3-ethyl-2-[2-(4-iminocyclohexa-2,5-dienylidene)-l-methylethylidene] benzothiazoline (XL), yellow crystals, m. 160°, λmaximum 3840 A. (ε 15,400). 2-Ethylbenzothiazole-EtI and XXXVII gave 18% XXXV (R = Me, R’ = Et), red crystals, m. 192° (decomposition), a trace of XXXVIII and, as above, the ethylimino analog of XL, m. 137° (from EtOH), λmaximum 3930 A. (ε 13,600). IV and Me2NC5H4CHO (XLI) gave 63% XXXV (R = Ph, R’ = Me), red crystals, m. about 180° (decomposition) (from AcOH). V and XLI gave 26% XXV (R = p-O2NC6H4, R’ = Et), terra cotta crystals, m. 203° (decomposition)(from MeOH) and the 1-(p-nitrophenyl)ethylidene analog of XL, yellow crystals, m. 220° (from Ac2O). VIII and XLI gave 24% XXXV (R = EtO2C, R’ = Me), orange crystals, m. 199° (decomposition) (from EtOH). XXXIIA and XLI gave 43% XXXV (R = 2-benzothiazolyl, R’ = Me), red crystals, m. 210° (decomposition) (from MeOH). To 2-methylbenzoxazole-p-MeC6H4SO3Et and XLI in hot EtOH was added Et3N, the whole refluxed 3 hrs., cooled, diluted with Et2O, the red tar separated, dissolved in MeOH, and the MeOH diluted with EtI in H2O gave 30% XXXVI (R = H, R’ = Me), red crystals, m. 251° (decomposition) (from EtOH). XV (1.52 g.) and XLI in Ac2O as above gave XXXVI (R = R’ = Me), red crystals, m. 210° (decomposition) (from MeOH). XVI and XLI gave XXXVI (R = Ph, R’ = Me), vermilion crystals, m. 223° (decomposition) (from EtOH). The effect of structure of these dyes on ultraviolet absorption as well as bathochromic shift is discussed.

Compound(6797-13-3)Formula: C9H9NO received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(2-Ethylbenzo[d]oxazole), if you are interested, you can check out my other related articles.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem