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

HRID 873619ノート

反応式

HRID 873619 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 442352773-(4-Methoxy-benzoyl)-benzenesulfonamide収率 50%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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): 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.

後処理

  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%)

出典と根拠

ORDレコード
ord-55c49f3819944bc6a26b8c66df515194
出典データセット
uspto-grants-2015_03
特許番号
US08975439B2

反応ノート

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