Veratroyl chloride → N-[2-chloro-5-(3-dimethylaminobenzamido)4-fluorophenyl]-3,4-dimethoxybenzamide

HRID 991429노트

반응식

HRID 991429 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[NH2:14][C:15]1[C:16]([Cl:34])=[CH:17][C:18]([F:33])=[C:19]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:31])[CH3:30])[CH:24]=2)[CH:20]=1>N1C=CC=CC=1>[Cl:34][C:16]1[CH:17]=[C:18]([F:33])[C:19]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:30])[CH3:31])[CH:24]=2)=[CH:20][C:15]=1[NH:14][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

참가 물질

4

반응물 2

HCID 77070Veratroyl chlorideHCID 22732310N-(5-amino-4-chloro-2-fluorophenyl)-3-dimethylaminobenzamide

생성물 1

HCID 9847600N-[2-chloro-5-(3-dimethylaminobenzamido)4-fluorophenyl]-3,4-dimethoxybenzamide수율 27.9%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 3,4-dimethoxybenzoyl chloride (0.5 g), N-(5-amino-4-chloro-2-fluorophenyl)-3-dimethylaminobenzamide (0.781 g) and pyridine (8 ml) was stirred at ambient temperature for 18 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and a saturated aqueous copper sulphate solution. The organic phase was washed in turn with water and a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica using a 99:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.328 g);

후처리

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. washThe organic phase was washed in turn with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica using
  7. additiona 99:1 mixture of methylene chloride and methanol as eluent

출처 및 근거

ORD 기록
ord-206ad1cdf15246a18208d54689358a07
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465455B1

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