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【结 构 式】

【分子编号】16857

【品名】3-iodo-4-isopropylbenzoyl chloride

【CA登记号】

【 分 子 式 】C10H10ClIO

【 分 子 量 】308.54597

【元素组成】C 38.93% H 3.27% Cl 11.49% I 41.13% O 5.19%

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)

Cariporide has been obtained by two similar ways: 1) The oxidation of 4-isopropylbenzaldehyde (I) with sodium perborate in hot acetic acid gives 4-isopropylbenzoic acid (II), which is sulfonated with hot chlorosufonic acid yielding 3-(chlorosulfonyl)-4-isopropylbenzoic acid (III). The reduction of (III) with sodium sulfite in hot NaOH solution affords 4-isopropyl-3-sulfinobenzoic acid (IV), which is alkylated with methyl bromide and NaOH in DMF giving 4-isopropyl-3-(methylsulfonyl)benzoic acid (V). The reaction of (V) with SOCl2 in refluxing toluene yields 4-isopropyl-3-(methylsulfonyl)benzoyl chloride (VI), which is finally condensed with guanidine (VII) in DMF. 2) The iodination of 4-isopropylbenzoic acid (II) with iodine chloride or N-iodosuccinimide (NIS) gives 3-iodo-4-isopropylbenzoic acid (VIII), which is treated first with SOCl2 to afford the corresponding acyl chloride (IX), and then with methanol yielding 4-iodo-4-isopropylbenzoic methyl ester (X). The reaction of (X) with sodium methylsulfite (XI) gives 4-isopropyl-3-(methylsulfonyl)benzoic acid methyl ester (XII), which is finally treated with guanidine (VII) in refluxing THF.

1 Graul, A.; Prous, J.; Castañer, J.; Cariporide Mesylate. Drugs Fut 1997, 22, 11, 1197.
2 Kleemann, H.-W.; Lang, H.-J.; Weichert, A.; Crause, P.; Scholz, W.; Albus, U.; Schwark, J.-R. (Aventis SA); Diacyl substd. guanidines, process for their preparation, their use as medicament or diagnostic reagent and medicament containing them. CA 2130703; DE 4328352; EP 0640587; JP 1995082234 .
3 Lang, H.-J.; Weichert, A.; Kleemann, H.-W.; Englert, H.; Scholz, W.; Albus, U. (Aventis SA); Benzoylguanidines, process for their preparation and their use as antiarrhythmic agents. EP 0589336; JP 1994228082; US 5591754 .
4 Kleemann, H.-W. (Aventis SA); Substd. benzoic acid esters, process for their preparation and their use for the synthesis of inhibitors of the cellular Na+/H+-exchange. DE 4428480 .
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) 23109 4-isopropylbenzaldehyde 122-03-2 C10H12O 详情 详情
(II) 11698 4-Isopropylbenzoic acid 536-66-3 C10H12O2 详情 详情
(III) 16851 3-(chlorosulfonyl)-4-isopropylbenzoic acid C10H11ClO4S 详情 详情
(IV) 16852 3-(dioxo-lambda(6)-sulfanyl)-4-isopropylbenzoic acid C10H12O4S 详情 详情
(V) 16853 4-isopropyl-3-(methylsulfonyl)benzoic acid C11H14O4S 详情 详情
(VI) 16854 4-isopropyl-3-(methylsulfonyl)benzoyl chloride C11H13ClO3S 详情 详情
(VII) 14790 Guanidine 113-00-8 CH5N3 详情 详情
(VIII) 16856 3-iodo-4-isopropylbenzoic acid C10H11IO2 详情 详情
(IX) 16857 3-iodo-4-isopropylbenzoyl chloride C10H10ClIO 详情 详情
(X) 16858 methyl 3-iodo-4-isopropylbenzoate C11H13IO2 详情 详情
(XI) 63963 sodium methanesulfinate CH3NaO2S 详情 详情
(XII) 16859 methyl 4-isopropyl-3-(methylsulfonyl)benzoate C12H16O4S 详情 详情
Extended Information