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

HRID 730209ノート

反応式

HRID 730209 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-68d54474a0174a71946368203176b6c4
出典データセット
uspto-grants-2009_09
特許番号
US07582673B2

反応ノート

読み込み中…