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【结 构 式】 
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【分子编号】43800 【品名】3-cyano-4-isobutoxybenzenecarbothioamide 【CA登记号】 |
【 分 子 式 】C12H14N2OS 【 分 子 量 】234.32204 【元素组成】C 61.51% H 6.02% N 11.96% O 6.83% S 13.68% |
与该中间体有关的原料药合成路线共 2 条
合成路线1
该中间体在本合成路线中的序号：(XII)The reaction of 4-nitrobenzonitrile (X) with KCN in hot DMSO, followed by treatment with isobutyl bromide (VI) and K2CO3, gives 4-isobutoxybenzene-1,3-dicarbonitrile (XI), which is treated with thioacetamide in hot DMF to yield 3-cyano-4-isobutoxythiobenzamide (XII). Cyclization of (XII) with 2-chloroacetoacetic acid ethyl ester (IV) in refluxing ethanol affords 2-(3-cyano-4-isoutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (IX), which is hydrolyzed with NaOH in hot THF/water.
| 【1】 Sorbera, L.A.; Castaner, J.; Rabasseda, X.; Revel, L.; TMX-67. Drugs Fut 2001, 26, 1, 32. |
| 【2】 Hasegawa, M.; A facile one-pot synthesis of 4-alkoxy-1,3-benzenedicarbonitrile. Heterocycles 1998, 47, 2, 857. |
| 【3】 Hasegawa, M.; Komoriya, K. (Teijin Ltd.); Cyano cpds. and their preparation method. JP 1994345724 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 21337 | ethyl 2-chloro-3-oxobutanoate | 609-15-4 | C6H9ClO3 | 详情 | 详情 |
| (VI) | 24599 | 1-bromo-2-methylpropane | 78-77-3 | C4H9Br | 详情 | 详情 |
| (IX) | 43797 | ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate | C18H20N2O3S | 详情 | 详情 | |
| (X) | 43798 | 4-nitrobenzonitrile | 619-72-7 | C7H4N2O2 | 详情 | 详情 |
| (XI) | 43799 | 4-isobutoxyisophthalonitrile | C12H12N2O | 详情 | 详情 | |
| (XII) | 43800 | 3-cyano-4-isobutoxybenzenecarbothioamide | C12H14N2OS | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)
| 【1】 Qi YM, Jie Q, Zhang FM.2009. Preparation of 2-(3-cyanophenyl) thiazole derivatives as xanthine oxidase inhibitors for treatment of hyperuricemia, hyperuricemia-induced gout, arthritis, or heart failure. Farming Zhuanli Shenqing Gongkai Shuomingshu, CN 101386604. |
| 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) | 60542 | ethyl 4-nitrobenzoate | 99-77-4 | C9H9NO4 | 详情 | 详情 |
| (II) | 67135 | ethyl 3-cyano-4-isobutoxybenzoate | C14H17NO3 | 详情 | 详情 | |
| (III) | 67136 | 3-cyano-4-isobutoxybenzamide | C12H14N2O2 | 详情 | 详情 | |
| (IV) | 43800 | 3-cyano-4-isobutoxybenzenecarbothioamide | C12H14N2OS | 详情 | 详情 | |
| (V) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
| (VI) | 43797 | ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate | C18H20N2O3S | 详情 | 详情 |
Extended Information