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【结 构 式】

【分子编号】26640

【品名】3-[(2,2,2-trifluoroacetyl)amino]benzoyl chloride

【CA登记号】

【 分 子 式 】C9H5ClF3NO2

【 分 子 量 】251.5921496

【元素组成】C 42.97% H 2% Cl 14.09% F 22.65% N 5.57% O 12.72%

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:(III)

The acylation of 3-aminobenzoic acid with acetic anhydride in ethyl acetate gives the corresponding acetamide (II), which is treated with SOCl2 in refluxing ethyl acetate yielding 3-(trifluoroacetamido)benzoyl chloride (III). The reaction of (III) with urea (IV) in toluene at 100 C gives the acylated urea (V), which is deprotected with butylamine in refluxing methanol to afford N-(3-aminobenzoyl)urea (VI). The acylation of (VI) with chloroacetyl chloride (VII) in dimethylacetamide provides the corresponding amide (VIII), which is finally treated with NaI in dimethylacetamide.

1 Bekesi, J.G.; Holland, J.F.; Jiang, J.-D.; Ma, L.; Roboz, J.; Deng, L.; Weisz, I.; Synthesis, cancericidal and antimicrotubule activities of 3-(haloacetamido)-benzoylureas. Anti-Cancer Drug Des 1998, 13, 7, 735.
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) 26638 3-Aminobenzoic acid 99-05-8 C7H7NO2 详情 详情
(II) 26639 3-[(2,2,2-trifluoroacetyl)amino]benzoic acid C9H6F3NO3 详情 详情
(III) 26640 3-[(2,2,2-trifluoroacetyl)amino]benzoyl chloride C9H5ClF3NO2 详情 详情
(IV) 19310 urea 57-13-6 CH4N2O 详情 详情
(V) 26641 N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2,2,2-trifluoroacetamide C10H8F3N3O3 详情 详情
(VI) 26642 N-(3-aminobenzoyl)urea C8H9N3O2 详情 详情
(VII) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(VIII) 26643 N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2-chloroacetamide C10H10ClN3O3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

3-Aminobenzoic acid (I) was protected as the trifluoroacetamide (II) using trifluoroacetic anhydride and then converted to acid chloride (III) by means of SOCl2. Subsequent condensation of (III) with urea provided 3-(trifluoroacetamido)benzoylurea (IV). After cleavage of the trifluoroacetamido group of (IV) by treatment with methanolic n-butylamine, the deprotected aniline (V) was coupled with bromoacetyl bromide in DMA to furnish the title bromoacetamide.

1 Bekesi, J.G.; Holland, J.F.; Jiang, J.-D.; Ma, L.; Roboz, J.; Deng, L.; Weisz, I.; Synthesis, cancericidal and antimicrotubule activities of 3-(haloacetamido)-benzoylureas. Anti-Cancer Drug Des 1998, 13, 7, 735.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
14005 2-Bromoacetyl bromide; Bromoacetyl bromide 598-21-0 C2H2Br2O 详情 详情
19310 urea 57-13-6 CH4N2O 详情 详情
(I) 26638 3-Aminobenzoic acid 99-05-8 C7H7NO2 详情 详情
(II) 26639 3-[(2,2,2-trifluoroacetyl)amino]benzoic acid C9H6F3NO3 详情 详情
(III) 26640 3-[(2,2,2-trifluoroacetyl)amino]benzoyl chloride C9H5ClF3NO2 详情 详情
(IV) 26641 N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2,2,2-trifluoroacetamide C10H8F3N3O3 详情 详情
(V) 26642 N-(3-aminobenzoyl)urea C8H9N3O2 详情 详情
Extended Information