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【结 构 式】

【分子编号】33251

【品名】5-acetyl-2-thiophenecarboxamide

【CA登记号】

【 分 子 式 】C7H7NO2S

【 分 子 量 】169.20412

【元素组成】C 49.69% H 4.17% N 8.28% O 18.91% S 18.95%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

The reaction of 5-carboxy-2-acetylthiophene (I) first with SOCl2 in refluxing toluene, and then with aqueous ammonia gives 5-carbamoyl-2-acetylthiophene (II), which is brominated with Br2 in hot acetic acid yielding 5-carbamoyl-2-bromoacetylthiophene (III). The cyclization of (III) with ammonium dithiocarbamate (A) in refluxing methanol-DMF affords 2-mercapto-4-(5'-carbamoyl-2'-thienyl)thiazole (IV), which is finally condensed with 1-chloro-3-tert-butylaminoisopropanol (V) by means of NaOH in water methanol.

1 Hara, Y.; et al.; Synthesis and beta-adrenergic blocking action of a new thiazolylthiopropanolamine derivative. J Pharm Sci 1978, 67, 1334-35.
2 Hibino, T.; et al.; JP 7525562 .
3 Hibino, T.; et al.; JP 7576069 .
4 Hibino, T.; et al. (Sumitomo Chemical Co., Ltd.); Thiazole derivatives. DE 2341753; FR 2196162; GB 1435139; NL 7311248; US 3932400 .
5 Reiner, A. (SkyePharma AG); Process for preparing ursodeoxycholic acid derivates and their inorganic and organic salts having therapeutic activity. EP 0272462 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 33253 ammonium carbamodithioate CH6N2S2 详情 详情
(I) 33250 5-acetyl-2-thiophenecarboxylic acid 4066-41-5 C7H6O3S 详情 详情
(II) 33251 5-acetyl-2-thiophenecarboxamide C7H7NO2S 详情 详情
(III) 33252 5-(2-bromoacetyl)-2-thiophenecarboxamide C7H6BrNO2S 详情 详情
(IV) 33254 5-(2-sulfanyl-1,3-thiazol-4-yl)-2-thiophenecarboxamide C8H6N2OS3 详情 详情
(V) 31720 1-(tert-butylamino)-3-chloro-2-propanol C7H16ClNO 详情 详情
Extended Information