Ammonia → 3-(4-Methoxy-benzoyl)-benzenesulfonamide

HRID 1515418노트

반응식

HRID 1515418 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([C:9]2[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:4]=1.[NH3:21]>ClCCl.CO>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([C:9]2[CH:10]=[C:11]([S:15]([NH2:21])(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 581074213-(4-Methoxy-benzoyl)-benzenesulfonyl chloride

생성물 1

HCID 442352773-(4-Methoxy-benzoyl)-benzenesulfonamide수율 50%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

3-(4-Methoxy-benzoyl)-benzenesulfonyl chloride is dissolved in dichloromethane (10 ml) and treated with 1.7 mL of a 2 M solution of ammonia in methanol. The reaction is stirred at ambient temperature for 2 hours and quenched with 1N HCl. The organic phase is separated and evaporated under reduced pressure to give the crude sulfonamide. Purification by silica gel chromatography (gradient of ethyl acetate in hexanes 5-25%) yielded 100 mg (50% yield) of the title compound. 1H NMR (CDCl3, 300 MHz): δ 8.3 (t, 1H, J=1.6 Hz), 8.1 (m, 1H), 7.95 (m, 1H), 7.8 (d, 2H, J=6.98 Hz), 7.65 (t, 1H, J=7.8 Hz), 7.0 (d, 2H, J=6.98 Hz), 4.95 (s, 2H), 3.9 (s, 3H). MP: 119-122° C. LCMS Elution time 0.81 MS (m/z): 291 (M+1). CHN Calc C, 57.72; H, 4.50; N, 4.81. Found C, 57.65; H, 4.33; N, 4.69

후처리

  1. customquenched with 1N HCl
  2. customThe organic phase is separated
  3. customevaporated under reduced pressure
  4. customto give the crude sulfonamide
  5. customPurification by silica gel chromatography (gradient of ethyl acetate in hexanes 5-25%)

출처 및 근거

ORD 기록
ord-167b9e479f0f4ac1b1ee7da7abec57bb
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222424B2

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