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【结 构 式】

【分子编号】39462

【品名】5-(2-chlorophenyl)-7-ethyl-1,3,5a,8a-tetrahydro-2H-thieno[2,3-e][1,4]diazepine-2-thione

【CA登记号】

【 分 子 式 】C15H15ClN2S2

【 分 子 量 】322.88228

【元素组成】C 55.8% H 4.68% Cl 10.98% N 8.68% S 19.86%

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)

Compound can be prepared in three different related ways: 1) The reaction of 5-(o-clorophenyl)-7-ethyl-3H-thieno[2,3-e]-1,4-diazepine-2-one (I) with P2S5 in pyridine at 80 C gives the corresponding thioketone (II), which by reaction with hydrazine hydrate (A) in methanol yields 2-hydrazino-5-(o-chlorophenyl)-7-ethyl-3H-thieno[2,3-e]-1,4-diazepine (III). Finally, this compound is cyclized with acetic anhydride acetic acid in refluxing benzene. This cyclization can also be carried out with refluxing ethyl orthoacetate (E) and H2SO4, with acetimino ethyl ether (G) in refluxing chloroform, with acetamidine hydrochloride (C) and 2-methylimidazole (D) at 160 C or thioacetamide (F) and H2SO4 at 190 C. 2) The condensation of thioketone (II) with acetohydrazide (B) in refluxing chloroform gives 2-acetylhydrazino-5-(o-chlorophenyl)-7-ethyl-3H-thieno[2,3-e]-1,4-diazepine (IV), which is then cyclized with acetic acid in refluxing benzene or by heating at 205 C. 3) The acetylated compound (IV) can also be obtained by acetylation of (III) with acetic anhydride and triethylamine at room temperature.

1 Nakanishi, M.; et al.; ZA 7204610 .
2 Thorpe, P.J.; Castaner, J.; Etizolam. Drugs Fut 1979, 4, 1, 22.
3 Nakanishi, M.; et al.; US 3904641 .
4 Tahara, T.; et al.; Syntheses and structure-activity relationship pf 6-aryl-4H-s-triazolo[3,4-c]thieno[2,3-e](1,4)diazepines. Arzneim-Forsch Drug Res 1978, 28, 7, 1153-58.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(G) 12831 ethyl ethanimidoate 1000-84-6 C4H9NO 详情 详情
(D) 15670 2-Methylimidazole; 2-Methyl-1H-imidazole 693-98-1 C4H6N2 详情 详情
(F) 19170 ethanethioamide 62-55-5 C2H5NS 详情 详情
(A) 27344 hydrazine 302-01-2 H4N2 详情 详情
(B) 29262 acetohydrazide 1068-57-1 C2H6N2O 详情 详情
(E) 39465 1-ethoxy-1,1-ethanediol C4H10O3 详情 详情
(I) 39461 5-(2-chlorophenyl)-7-ethyl-1,3-dihydro-2H-thieno[2,3-e][1,4]diazepin-2-one C15H13ClN2OS 详情 详情
(II) 39462 5-(2-chlorophenyl)-7-ethyl-1,3,5a,8a-tetrahydro-2H-thieno[2,3-e][1,4]diazepine-2-thione C15H15ClN2S2 详情 详情
(III) 39463 5-(2-chlorophenyl)-7-ethyl-2-hydrazino-3H-thieno[2,3-e][1,4]diazepine C15H15ClN4S 详情 详情
(IV) 39464 N'-[5-(2-chlorophenyl)-7-ethyl-3H-thieno[2,3-e][1,4]diazepin-2-yl]acetohydrazide C17H17ClN4OS 详情 详情
(C) 15866 ethanimidamide C2H6N2 详情 详情
Extended Information