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【结 构 式】

【分子编号】11909

【品名】5-Chloro-2-nitrophenylhydrosulfide; 5-Chloro-2-nitrobenzenethiol

【CA登记号】

【 分 子 式 】C6H4ClNO2S

【 分 子 量 】189.622

【元素组成】C 38.01% H 2.13% Cl 18.7% N 7.39% O 16.88% S 16.91%

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:(I)

A new synthesis of racemic TA-3090 has been reported: The condensation of 5-chloro-2-nitrothiophenol (I) with 4-methoxybenzyl chloride (II) by means of sodium ethoxide in ethanol gives the thioether (III), which is reduced with SnCl2 in hot ethanol to afford 4-chloro-2-(4-methoxybenzylthio)aniline (IV). The acylation of (IV) with ethoxalyl chloride (V) by means of NaHCO3 in dichloromethane - water yields the oxamate (VI), which is condensed with 2-(dimethylamino)ethyl chloride (VII) by means of K2CO3 and 18-crown-6 in hot acetonitrile to afford the alkylated oxamate compound (VIII). The cyclization of (VIII) by means of lithium diisopropylamide in THF gives 8-chloro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-1,5-benzothiaze pine-3,4(2H,5H)-dione (IX), which is reduced with NaBH4 in aqueous ethanol to cis-8-chloro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one (X). Finally, this compound is acetylated in the usual manner.

1 Takeda, M.; Takamura, N.; Oh-ishi, T.; Harada, T.; Morimoto, M.; Inoue, H.; Nagasawa, M.; A new synthetic route to 1,5-benzothiazepines. Synthesis of derivatives of diltiazem. Chem Pharm Bull 1992, 40, 8, 1986.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11909 5-Chloro-2-nitrophenylhydrosulfide; 5-Chloro-2-nitrobenzenethiol C6H4ClNO2S 详情 详情
(II) 11910 4-Methoxybenzyl chloride; 1-(Chloromethyl)-4-methoxybenzene; alpha-Chloro-4-methoxytoluene; 4-(Chloromethyl)phenyl methyl ether 824-94-2 C8H9ClO 详情 详情
(III) 11911 4-[[(5-Chloro-2-nitrophenyl)sulfanyl]methyl]phenyl methyl ether; 4-Chloro-2-[(4-methoxybenzyl)sulfanyl]-1-nitrobenzene C14H12ClNO3S 详情 详情
(IV) 11912 4-Chloro-2-[(4-methoxybenzyl)sulfanyl]phenylamine; 4-Chloro-2-[(4-methoxybenzyl)sulfanyl]aniline C14H14ClNOS 详情 详情
(V) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(VI) 11914 ethyl 2-[4-chloro-2-[(4-methoxybenzyl)sulfanyl]anilino]-2-oxoacetate C18H18ClNO4S 详情 详情
(VII) 11907 Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine 107-99-3 C4H10ClN 详情 详情
(VIII) 11916 ethyl 2-[4-chloro[2-(dimethylamino)ethyl]-2-[(4-methoxybenzyl)sulfanyl]anilino]-2-oxoacetate C22H27ClN2O4S 详情 详情
(IX) 11917 (2S)-8-Chloro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione C20H21ClN2O3S 详情 详情
(X) 11908 (2S,3S)-8-Chloro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one C20H23ClN2O3S 详情 详情
Extended Information