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【结 构 式】

【分子编号】32940

【品名】2-(5-ethyl-1-benzothiophen-3-yl)ethylamine; 2-(5-ethyl-1-benzothiophen-3-yl)-1-ethanamine

【CA登记号】

【 分 子 式 】C12H15NS

【 分 子 量 】205.32384

【元素组成】C 70.2% H 7.36% N 6.82% S 15.62%

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:(IX)

Thiol (II) was prepared by reduction of 4-ethylbenzenesulfonyl chloride (I) with LiAlH4. Subsequent alkylation of (II) with ethyl 4-chloroacetoacetate (III) provided sulfide (IV), which was cyclized to the required benzothiophene (V) on heating with polyphosphoric acid in toluene. Basic hydrolysis of the ester group of (V) gave carboxylic acid (IV). After conversion of (VI) to the corresponding acid chloride with SOCl2, treatment with NH4OH yielded amide (VII). This was dehydrated to nitrile (VIII) using trifluoroacetic anhydride and triethylamine. Reduction of the nitrile function of (VIII) by means of LiAlH4 and AlCl3 gave rise to the corresponding primary amine, which was isolated as the hydrochloride salt (IX). Finally, acylation with acetyl chloride furnished the title acetamide.

1 Lesieur, D.; Fourmaintraux, E.; Depreux, P.; Delagrange, P.; Renard, P.; Guardiola-Lemaître, B. (ADIR et Cie.); Alkyl(hetero)cyclic cpds., process for their preparation and pharmaceutical compsns. containing them. CA 2167039; CA 2167040; EP 0721938; EP 0721947; FR 2729147; JP 1996231530; JP 1996239353; US 5693665; US 5703121; US 5780512 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
19273 acetyl chloride 75-36-5 C2H3ClO 详情 详情
(I) 26619 4-ethylbenzenesulfonyl chloride 16712-69-9 C8H9ClO2S 详情 详情
(II) 32934 4-ethylbenzenethiol; 4-ethylphenylhydrosulfide 4946-13-8 C8H10S 详情 详情
(III) 23541 ethyl 4-chloro-3-oxobutanoate;Ethyl 4-chloro-3-oxobutanoate;Ethyl 4-chloroacetoacetate 638-07-3 C6H9ClO3 详情 详情
(IV) 32935 ethyl 4-[(4-ethylphenyl)sulfanyl]-3-oxobutanoate C14H18O3S 详情 详情
(V) 32936 ethyl 2-(5-ethyl-1-benzothiophen-3-yl)acetate C14H16O2S 详情 详情
(VI) 32937 2-(5-ethyl-1-benzothiophen-3-yl)acetic acid C12H12O2S 详情 详情
(VII) 32938 2-(5-ethyl-1-benzothiophen-3-yl)acetamide C12H13NOS 详情 详情
(VIII) 32939 2-(5-ethyl-1-benzothiophen-3-yl)acetonitrile C12H11NS 详情 详情
(IX) 32940 2-(5-ethyl-1-benzothiophen-3-yl)ethylamine; 2-(5-ethyl-1-benzothiophen-3-yl)-1-ethanamine C12H15NS 详情 详情
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