Month: June 2021

151230-42-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6-Bromo-2-methylbenzo[d]oxazole, cas is 151230-42-1,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of Compound 24 (480 mg, 2.264 mmol) in 1,4-dioxane (7 mL) were added TETRAKIS(TRIPHENYLPHOSPHINE) PALLADIUM (0) (183 mg, 0.158 mmol), PHENYLBORONIC ACID (414 mg, 3.40 mmol) and 2M aqueous potassium phosphate solution (3.4 ml, 6.8 mmol) under nitrogen atmosphere at room temperature, then the reaction mixture was stirred at 150 C. for 40 minutes under microwave irradiation. To the reaction solution was added 1N hydrochloric acid, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by column chromatography to give Compound 25 (385 mg, 81%).Compound 25; 1H-NMR (DMSO-d6) delta: 2.64 (s, 3H), 7.38 (dd, J=8.4, 2.0 Hz, 1H), 7.47-7.51 (m, 2H), 7.64 (d, J=2.0 Hz, 1H), 7.77-7.75 (m, 3H), 7.96 (s, 1H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6-Bromo-2-methylbenzo[d]oxazole, 151230-42-1

Reference：
Patent; Shionogi & Co., Ltd.; US2012/253040; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

19932-85-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6-Bromobenzo[d]oxazol-2(3H)-one, 19932-85-5

Reference：
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

864274-04-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2-Methylbenzo[d]oxazole-6-carbaldehyde, cas is 864274-04-4,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To the solution of 2-(2,6 dichloro-phenylimino)-thiazolidin-4-one (483 mg, 1.85 mmol) in acetic acid (8 mL) was added 2-methyl-benzooxazole-6-carbaldehyde (300 mg, 1.85 mmol, 1 eq) followed by sodium acetate (0.8 g). The reaction mixture was refluxed for 48 hours and water (10 mL) was added. Solid was filtered and purified by column chromatography (1 :5 ethyl acetate:dichloromethane) to give 1 10 mg (15 percent yield) of pure 2-(2,6-dichloro-phenylimino)-5-(2-methyl-benzooxazol-6-yl- methylene)-thiazolidin-4-one. 1H-NMR (CDCI3): D2.69 (s, 3H), 7.12 (t, 1 H, J=8.1 Hz), 7.36 (d, 3H, J=7.8 Hz), 7.56 (s, 1 H), 7.70 (d, 1 H, J=8.1 Hz), 7.88 (s, 1 H), 9.69 (s, 1 H). LC MS (m/e) = 404.0 (MH+). Rt = 2.36 min.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-Methylbenzo[d]oxazole-6-carbaldehyde, 864274-04-4

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/103755; (2007); A2;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 5-Bromobenzo[d]oxazole, cas is 132244-31-6 its synthesis route is as follows.

To a solution of 5-bromobenzo[d]oxazole (1.2 g, 6.06 mmol, 1 eq.) in DMF (10 mL) was added 5-(4,4,5,5-Bis(pinacolato)diboron (1.68 g, 1.66 mmol, 1.1 eq.), KOAc (1.7 g, 18.09 mmol, 3 eq.), and PdCl2(dppf)?DCM complex (247 mg, 0.23 mmol, 0.05 eq.). The reaction mixture was deoxygenated with N2 and the reaction mixture was stirred at 80 C. for 18 h. The progress of the reaction was monitored by LCMS The reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with ethyl acetate (2*50 mL). Combined organic layer was washed with brine (20 mL) and dried over sodium sulfate. Removal of solvent under reduced pressure gave crude which was purified by flash chromatography(0-100% Hexane-EtOAc) to afford 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (0.900 g, 60%) as off white solid. LCMS: 245, 247 [M+1]+

132244-31-6, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,132244-31-6 ,5-Bromobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (120 pag.)US2019/23666; (2019); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

4570-41-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Benzo[d]oxazol-2-amine, cas is 4570-41-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 4-chloro-6-methylpyrimidin-2-amine (1)(1 mmol) in dry ethanol (4 ml), benzoxazol-2-amine (2a)/benzothiazol-2-amine (2b)/1H-benzimidazol-2-amine (2c)(1.1 mmol) and a catalytic amount of methanesulfonic acid(0.2 ml) were added and refluxed for 5?7 h. After completionof the reaction the contents were cooled and dilutedwith water (15 ml). The separated solid was filtered, washedwith water, dried and recrystallized from 2-propanol. N4-(1,3-Benzoxazol-2-yl)-6-methyl-2,4-pyrimidinediamine(4a)Red solid; yield 74percent; m.p. 138?140 °C; IR (KBr) vmax 3478(NH2), 3381, 3320 (NH), 1578 (C=N) cm?1; 1H NMR(DMSO?d6, 400 MHz): delta = 2.47 (s, 3H, CH3), 7.01 (s, 1H,C5?H), 7.12 (s, 2H, NH2), 7.33?7.49 (m, 4H, Ar?H), 8.27(bs, 1H, NH); 13C NMR (DMSO?d6, 100 MHz): delta = 24.9(CH3), 96.1 (C?5), 160.4 (C?2?), 164.4 (C?2), 167.5 (C?6),171.9 (C?4), 112.3, 121.6, 125.9, 126.7, 143.4, 152.5(aromatic carbons); MS (m/z): 241.25 [M+]. Anal. Calcd.for C12H11N5O: C, 59.74; H, 4.60; N, 29.03. Found: C,59.86; H, 4.62; N; 29.24.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4570-41-6, Benzo[d]oxazol-2-amine

Reference：
Article; Seenaiah, Dandu; Rekha, Tamatam; Padmaja, Adivireddy; Padmavathi, Venkatapuram; Medicinal Chemistry Research; vol. 26; 2; (2017); p. 431 – 441;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 5-Chlorobenzo[d]oxazole-2(3H)-thione, and cas is 22876-19-3, its synthesis route is as follows.

Thiol 9a (10.5 kg, 54.6 mol) was added to a vessel and suspended in DCM (141 kg). Oxalyl chloride (10.4 kg, 82.3 mol) was added (slightly endothermic) followed by DMF (40.0 kg, 547 mol) over 1.25 h, such that the batch temperature was 25 C. The batch was aged at 20 C. forapproximately 30 mi HPLC analysis showed reaction to becomplete. The batch was cooled to 10 C. then triethylamine (16.64 kg, 164.4 mol) was added via a sub-surface sampleline at such a rate as to maintain a batch temperature of 10C. A sub-surface addition protocol was required to preventbuild up of triethylamine hydrochloride solid on the walls ofthe vessel. The batch was cooled to 00 C., then a solution ofN-l3oc-ethylenediamine (10.5 kg, 61.2 mol)inDCM(lOkg)was added such that the batch temperature was 10 C. Thereaction was warmed to 20 C. and stirred for 2.5 h, HPLCanalysis showed the reaction to be complete. Water (63.6 kg)was charged to the batch and the mixture stirred for 5 mm.The layers were separated and the aqueous phase re-extracted with DCM (42.2 kg). The organic solutions werethen combined and approximately half of the total DCMvolume was distilled from the batch under vacuum whilstmaintaining a temperature of 40 C. MeCN (83.3 kg) wasthen added and the remaining DCM removed by distillation(0.5 mol % DCM left by ?H NMR wrt MeCN). MVK (4.61kg, 65.8 mol) was added to the batch followed by DI3U (4.17kg, 27.4 mol) such that the temperature was 20 C. Thebatch was aged for 10 h at 20 C. then analyzed by HPLC.The reaction was then diluted with water (42.4 kg) and agedfor a further 30 mm. The mixture was filtered and the slurrywashed with MeCN (33.3 kg). The solid was washed withMeCN (.-10 L) then dried in a vacuum oven (T=60 C.) for22 h. MVK adduct 10 (15.5 kg) was isolated as an off-whitesolid. mp 145-148 C. ?H NMR (400 MHz, CDC13): oe 7.24(d, 1H, J=2.3 Hz), 7.09 (d, 1H, J=8.5 Hz), 6.91 (dd, 1H,J=8.5, 2.3 Hz), 5.06 (s, 1H, br), 3.73 (t, 2H, J=6.7 Hz), 3.63(t, 2H, J=6.1 Hz), 3.37 (d, 2H, br), 2.89 (t, 2H, J=6.7 Hz),2.14 (s, 3H), 1.33 (s, 9H). ?3C NMR (100.6 MHz, CDC13):206.7, 163.0, 156.0, 147.4, 144.6, 129.2, 120.3, 116.6,109.2, 79.4, 49.3, 44.3, 41.9, 39.1, 30.2, 28.3. HRMS (ESI):mlz [M+H] calcd for C,8H24C1N304: 382.1534; found:

22876-19-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,22876-19-3 ,5-Chlorobenzo[d]oxazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see

Reference：
Patent; MERCK SHARP & DOHME CORP.; Fleitz, Fred; Mangion, Ian; Yin, Jingjun; (11 pag.)US9441254; (2016); B2;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is Benzo[d]oxazole-2-thiol, and cas is 2382-96-9, its synthesis route is as follows.

Example 2 (Compound No. 8 in Table) Production of 9-(benzoxazol-2-ylthio)-N-(2-methylthio-3-pyridyl)nonanamide: The reaction and the treatment were conducted in the same manner as in Example 1 except that 9-bromononanoyl chloride was used instead of 6-bromohexanoyl chloride to obtain 9-bromo-N-(2-methylthio-3-pyridyl)nonanamide. To a DMF (5 ml) solution of this amide (90 mg, 0.25 mmol) and 2-mercaptobenzoxazole (38 mg, 0.25 mmol) were added potassium carbonate (42 mg, 0.30 mmol) and 18-crown-6 (7 mg, 0.03 mmol), and the mixture was stirred at 80C for 3 hours. The reaction mixture was allowed to cool, and then extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting residue was recrystallized from a mixture of ethyl acetate-hexane to obtain 83 mg (yield 77%) of the desired compound as a colorless powdery crystal. Melting point: 84 – 85C IR (KBr) cm-1:3465, 3276, 2926, 1664, 1505.

2382-96-9, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,2382-96-9 ,Benzo[d]oxazole-2-thiol, other downstream synthetic routes, hurry up and to see

Reference：
Patent; KOWA COMPANY LTD.; EP979823; (2000); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

59-49-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2-Benzoxazolinone, cas is 59-49-4,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Intermediates 10-17 were prepared following literature methods [49] with slight modifications. 2-Benzoxazolone 8 or 2-benzothiazolone 9 (7.4mmol), appropriate 1-omega-dibromoalkane (8mmol), potassium carbonate (8mmol) and acetone (10mL) were refluxed for 4h and then allowed to stand at room temperature. The mixture was filtered to eliminate inorganic material and then evaporated under reduced pressure to obtain a residue, which was taken up in water. The solution was extracted with dichloromethane (3×50 mL) and the combined extracts were washed with water, dried, and evaporated. The residue was triturated twice with light petroleum ether 40-60C to give intermediates 10-17 that were used without further purification in the subsequent steps. Analytical and spectral data are reported only for unknown compounds 13 and 17.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-Benzoxazolinone, 59-49-4

Reference：
Article; Salerno, Loredana; Pittala, Valeria; Modica, Maria N.; Siracusa, Maria A.; Intagliata, Sebastiano; Cagnotto, Alfredo; Salmona, Mario; Kurczab, Rafa?; Bojarski, Andrzej J.; Romeo, Giuseppe; European Journal of Medicinal Chemistry; vol. 85; (2014); p. 716 – 726;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 2-(Bromomethyl)benzo[d]oxazole, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 73101-74-3, its synthesis route is as follows.

EXAMPLE 5 Various compounds of the formula: STR10 as listed in the following Table 4 were prepared in substantially the same manner as in Examples 3 and 4. example 6 benzoxazole-2-methanesulfonyl chloride: To a solution of 3.0 g of 2-bromomethylbenzoxazole [prepared according to the procedures described in Belgian Pat. No. 624,463] in 40 ml of methanol was added a solution of 1.9 g of sodium sulfite in 40 ml of water. The mixture was heated with stirring at 60 C. for 6 hours and concentrated under reduced pressure to give crude sodium benzoxazole-2-methanesulfonate (4.5 g).

73101-74-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,73101-74-3 ,2-(Bromomethyl)benzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Dainippon Pharmaceutical Co., Ltd.; US4172896; (1979); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 5-Chlorobenzo[d]oxazole-2(3H)-thione, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 22876-19-3, its synthesis route is as follows.

Oxalyl chloride (1.20 g, 9.4 mmol) was added dropwise to a stirred suspension of 2- mercapto-5-chlorobenzoxazol (1.28 g, 6.9 mmol) in CH2C12 (37 mL) at < 20C. DMF (4.59 g, 62.8 mmol) was added dropwise. A vigorous gas formation was observed and the suspension turned into a solution halfway throughout the addition. The reaction mixture was stirred for 20 minutes. Two additional aliquots oxalyl chloride (1 : 0.20g, 1.35 mmol; 2: 0.40 g, 2.70 mmol) were added and the reaction mixture was stirred for 1.5 hours. HPLC indicated complete conversion of 2-mercapto-5-chlorobenzoxazol into 2,5- Dichlorobenzoxazol . 22876-19-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,22876-19-3 ,5-Chlorobenzo[d]oxazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see

Reference：
Patent; SANDOZ AG; BARTH, Roland; HOeFERL-PRANTZ, Kathrin; RICHTER, Frank; WIDSCHWENTER, Gerhard; (166 pag.)WO2016/20405; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem