(4-Nitrophenyl)methanesulfonamide → 1-(4-Aminophenyl)methanesulfonamide

HRID 583910노트

반응식

HRID 583910 반응식
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([NH2:12])(=[O:10])=[O:11])=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 2755281(4-Nitrophenyl)methanesulfonamideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 108214071-(4-Aminophenyl)methanesulfonamide수율 97.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매

실험 절차

To 10% palladium on charcoal catalyst (3 g, 50% wet with water) under a nitrogen atmosphere was added a solution of 4-nitro-benzylsulfonamide (17.53 g, 81.1 mmol). in dimethylformamide (175 ml). The atmosphere of nitrogen was replaced with hydrogen and the mixture stirred vigourously for 5 h. The atmosphere was replaced with nitrogen and the mixture filtered through celite. The solvent was removed in vacuo and the residue triturated with diethylether to give a dark brown solid (14.7 g). The solid was heated in acetonitrile (440 ml) and filtered whilst hot (to remove excess catalyst). The filtrate was allowed to cool and the precipitate filtered off and dried in vacuo to give the title compound as a beige solid (12.32 g, 82%). δH [2H6]—DMSO 4.05 (2H, s); 5.11 (2H, s); 6.53 (2H, d, 8.2 Hz); 6.63 (2H, s); 7.01(2H,d, 8.2 Hz).

후처리

  1. filtrationthe mixture filtered through celite
  2. customThe solvent was removed in vacuo
  3. customthe residue triturated with diethylether

출처 및 근거

ORD 기록
ord-9bbd69963680421094a9a4471d347832
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924297B2

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