3-Nitrobenzenesulfonyl chloride → 2-methoxy-N-[2-(3-nitrobenzenesulfonylamino)phenyl]-5-trifluoromethanesulfonylbenzenesulfonamide

HRID 730209노트

반응식

HRID 730209 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]=[C:16]([S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:25][CH3:26])(=[O:11])=[O:10].[N+:27]([C:30]1[CH:31]=[C:32]([S:36](Cl)(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]>C(Cl)Cl.N1C=CC=CC=1>[CH3:26][O:25][C:13]1[CH:14]=[CH:15][C:16]([S:18]([C:21]([F:24])([F:22])[F:23])(=[O:20])=[O:19])=[CH:17][C:12]=1[S:9]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:36]([C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([N+:27]([O-:29])=[O:28])[CH:31]=1)(=[O:37])=[O:38])(=[O:10])=[O:11]

참가 물질

5

반응물 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 68948452N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamide

생성물 1

HCID 689481802-methoxy-N-[2-(3-nitrobenzenesulfonylamino)phenyl]-5-trifluoromethanesulfonylbenzenesulfonamide수율 87.3%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamide (2 mmol, prepared as in Example A) in DCM (4 mL) and pyridine (4 mL), 3-nitrobenzenesulfonyl chloride (2.2 mmol) was added at RT and the reaction mixture was then allowed to stir at RT. The reaction mixture was then diluted with DCM (20 mL). The organic phase was washed with 10% aqueous HCl (20 mL), water (20 mL) and brine (20 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 afford 1.04 g of 2-methoxy-N-[2-(3-nitrobenzenesulfonylamino)phenyl]-5-trifluoromethanesulfonylbenzenesulfonamide. LC: Tr 1.17 min, MS: 596.6 (M+1)+. 1H NMR (CDCl3, 400 MHz): δ 4.27 (s, 3H), 6.76 (d, 1H), 6.78(bs, 1H), 7.05 (m, 1H), 7.16 (m, 2H), 7.34 (d, 1H), 7.68 (bs, 1H), 7.72 (t, 1H), 8.01 (dd, 1H), 8.20 (dd, 1H), 8.25 (d, 1H), 8.46 (dd, 1H), 8.55 (d, 1H) ppm.

후처리

  1. washThe organic phase was washed with 10% aqueous HCl (20 mL), water (20 mL) and brine (20 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-68d54474a0174a71946368203176b6c4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582673B2

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