【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% |
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 |