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【结 构 式】

【分子编号】22165

【品名】2-(3-benzoyl-2-methyl-1-azulenyl)ethanethioamide

【CA登记号】

【 分 子 式 】C20H17NOS

【 分 子 量 】319.42712

【元素组成】C 75.2% H 5.36% N 4.38% O 5.01% S 10.04%

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)

Friedel Crafts acylation of methyl 2-methylazulene-1-carboxylate (I) with benzoyl chloride (II) and AlCl3 yielded the benzoylazulene (III). Subsequent saponification of the ester function with NaOH, followed by decarboxylation of the resulting acid (IV) using p-TsOH in boiling benzene provided (V). Mannich reaction of (V) with bis(dimethylamino)methane and paraformaldehyde produced amine (VI), which was quaternized with MeI to furnish the ammonium salt (VII). This was displaced by ethanolic KCN to give nitrile (VIII). Thioamide (IX) was then obtained by reaction of (VIII) with thioacetamide and HCl. Finally, the thiazole ring was constructed by cyclization of (IX) with bromoacetone.

1 Tomiyama, T.; Kasai, R.; Takeuchi, S.; Onkura, Y.; Benzoylazulene derivatives as selective cyclooxygenase-2 inhibitors. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 170.
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) 22157 methyl 2-methyl-1-azulenecarboxylate C13H12O2 详情 详情
(III) 22159 methyl 3-benzoyl-2-methyl-1-azulenecarboxylate C20H16O3 详情 详情
(IV) 22160 3-benzoyl-2-methyl-1-azulenecarboxylic acid C19H14O3 详情 详情
(V) 22161 (2-methyl-1-azulenyl)(phenyl)methanone C18H14O 详情 详情
(VI) 22162 [3-[(dimethylamino)methyl]-2-methyl-1-azulenyl](phenyl)methanone C21H21NO 详情 详情
(VII) 22163 [2-methyl-3-[(trimethyl-lambda(5)-azanyl)methyl]-1-azulenyl](phenyl)methanone C22H25NO 详情 详情
(VIII) 22164 2-(3-benzoyl-2-methyl-1-azulenyl)acetonitrile C20H15NO 详情 详情
(IX) 10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
(IX) 22165 2-(3-benzoyl-2-methyl-1-azulenyl)ethanethioamide C20H17NOS 详情 详情
Extended Information