N-(2-aminophenyl)-4-chlorobenzenesulfonamide → 2-chloro-N-[2-(4-chloro-benzenesulfonylamino)phenyl]-5-trifluoromethylbenzenesulfonamide

HRID 730228노트

반응식

HRID 730228 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.N1C=CC=CC=1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:22][C:21]=1[S:30]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])(=[O:32])=[O:31]

참가 물질

5

반응물 2

HCID 241359N-(2-aminophenyl)-4-chlorobenzenesulfonamideHCID 27342742-Chloro-5-(trifluoromethyl)benzene-1-sulfonyl chloride

생성물 1

HCID 689490302-chloro-N-[2-(4-chloro-benzenesulfonylamino)phenyl]-5-trifluoromethylbenzenesulfonamide수율 79.8%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-(2-amino-phenyl)-4-chlorobenzenesulfonamide (1.0 mmol, prepared as in Example 11) in DCM (2 mL) and pyridine (2 mL), 2-chloro-5-(trifluoromethyl)benzenesulfonyl chloride (1.1 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (10 mL). The organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL), and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to obtain 419 mg of 2-chloro-N-[2-(4-chloro-benzenesulfonylamino)phenyl]-5-trifluoromethylbenzenesulfonamide. LC: Tr 1.25 min; MS: 525.9 (M+1).

후처리

  1. washThe organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL), and brine (10 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM/EtOAc

출처 및 근거

ORD 기록
ord-7e7285c4c6c849808e8ba9c99bdcbcac
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582673B2

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