O-Phenylenediamine → N-(2-aminophenyl)-4-chlorobenzenesulfonamide

HRID 730213노트

반응식

HRID 730213 반응식
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)Cl.N1C=CC=CC=1>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][S:16]([C:13]1[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=1)(=[O:18])=[O:17]

참가 물질

5

반응물 2

HCID 7243O-PhenylenediamineHCID 73984-Chlorobenzenesulfonyl chloride

생성물 1

HCID 241359N-(2-aminophenyl)-4-chlorobenzenesulfonamide수율 84.9%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of o-phenylenediamine (4 mmol) in DCM (20 mL) and pyridine (4 mL) at 0° C., 4-chlorobenzenesulfonyl chloride (4.4 mmol) was added in small portions. The reaction mixture was then gradually warmed to RT with stirring continued until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with DCM (20 mL). The organic phase was washed with water (2×20 mL) and 20 mL of brine. 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 give 960 mg of N-(2-aminophenyl)-4-chlorobenzenesulfonamide. LC: Tr 0.92 min, MS: 284.0 (M+1)+.

후처리

  1. washThe organic phase was washed with water (2×20 mL) and 20 mL of brine
  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-8df9621de0e3434b970c652dd0018076
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582673B2

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