Pyridine → N-(4-acetylphenyl)methanesulfonamide

HRID 10720

반응식

HRID 10720 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].N1C=CC=CC=1.[S:17](Cl)([CH3:20])(=[O:19])=[O:18]>ClCCl>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7468p-AminoacetophenoneHCID 31297Methanesulfonyl chloride

생성물 1

HCID 684083N-(4-acetylphenyl)methanesulfonamide수율 60%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ex-100A: A solution of 4-aminoacetophenone (5.0 g, 37.0 mmol) and pyridine (3.0 mL) in anhydrous dichloromethane (300 mL) was treated with mesyl chloride (2.86 mL, 37.0 mmol). The reaction was stirred for 84 hours at room temperature under nitrogen, and then quenched with saturated NH4Cl solution (100 mL). The organic phase was collected, washed with water (100 mL) and brine, dried over sodium sulfate, and concentrated over silica. The material was purified by silica gel chromatography (50% ethyl acetate/hexanes) to give 4.72 g (60%) of N-(4-acetyl-phenyl)-methanesulfonamide as a yellowish oil. 1H-NMR (DMSO-d6) δ 10.28 (s, 1H), 7.90 (d, 1H), 7.24 (d, 1H), 3.06 (s, 3H), 2.48 (s, 3H).

후처리

  1. customquenched with saturated NH4Cl solution (100 mL)
  2. customThe organic phase was collected
  3. washwashed with water (100 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated over silica
  6. customThe material was purified by silica gel chromatography (50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-4e657d09667144e7a75208f9bb28d3d5
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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