The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthetic anticonvulsants. Preparation and properties of some benzoxazoles》. Authors are Bywater, W. G.; Coleman, W. R.; Kamm, Oliver; Merritt, H. Houston.The article about the compound:2-Ethylbenzo[d]oxazolecas:6797-13-3,SMILESS:CCC1=NC2=CC=CC=C2O1).Quality Control of 2-Ethylbenzo[d]oxazole. Through the article, more information about this compound (cas:6797-13-3) is conveyed.
The following benzoxazoles were prepared by heating mol. equivalents of tech. o-H2NC6H4OH and the appropriate acid, amide, or nitrile to boiling for several hrs.; the reaction mixture was distilled at atm. pressure and the crude product, if liquid, was dissolved in petr. ether and washed with 10% NaOH, which destroyed the characteristic fluorescence of the crude material. The solids were pulverized and washed with 10% alkali and H2O before crystallizing from dilute EtOH or Me2CO. The m.ps. and b.ps. are corrected AmCO2H gives 67.2% of 2-amylbenzoxazole, b2 125°, b. 264-6°; Et2CHCO2H gives 44.3% of the (1-ethylpropyl) analog, b1 110°, b. 250-2°; caprylic acid yields 61.5% of the heptyl analog, b4 174-5°, b. 294-8°; lauramide yields 30% of the hendecyl analog, b1 179-84°, b. 347-53°, m. 32-3°; oleic acid gives 38.6% of the 8-heptadecenyl analog, b2 248-9°; Ph2CHCO2H yields 55.1% of the (diphenylmethyl) analog, m. 69.5-70.5°; (CH2CO2H)2 gives 44.5% of 2,2′-ethylenedibenzoxazole, m. 194.5-5.5°. The following yields (%) were obtained of known 2-alkyl derivatives of benzoxazole: Et 50, hexyl 71.4, pentadecyl 26, heptadecyl 27.7, Ph 33.3, PhCH2 82.4 (from PhCH2CO2H), 40.6 (from PhCH2CN), p-ClC6H4 30.5, HO 35, styryl 4 [in this reaction a by-product b14 87-9° (HCl salt, m. 154-5°, N 8.2%, Cl 20.38%)]. Benzoxazolone results in 35% yield by fusing CO(NH2)2 with tech. o-H2NC6H4OH at 200°; BuNHCONH2 gives 10.2%; urethan gives 53%. Anticonvulsant activity [A, if the convulsive threshold is elevated to more than 50 ma., B, if increased by 20-30 ma. 2 hrs. after treatment; the figure is the dose (g./kg.) at which the rating was established] of 2-substituted benzoxazoles was determined as follows: Me, A, 0.5; Et, B, 0.37; Am, B, 0.15; (1-ethylpropyl), B, 0.25; hexyl, B, 1.0; heptyl, A, 0.38; pentadecyl, B, 0.41; benzyl, A, 0.3; benzimidazole, A, 0.47; dilantin Na, A, 0.05. Toxicity data (LD40) in g./kg. (white mice, orally): HO 0.94, Me 1.10, Et 1.0, Am 1.3, (1-ethylpropyl) 1.3, hexyl 2.75, heptyl 2.3, pentadecyl 5+, heptadecyl 10.5+, Ph 5+, benzyl 1.75, (p-chlorophenyl) 6, (diphenylmethyl) 0.05, 2-aminobenzimidazole 0.60, dilantin Na 0.5.
This compound(2-Ethylbenzo[d]oxazole)Quality Control of 2-Ethylbenzo[d]oxazole was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.
Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem