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

HRID 1515418Notes

Reaction equation

HRID 1515418 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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

Workup

  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%)

Sources & evidence

ORD record
ord-167b9e479f0f4ac1b1ee7da7abec57bb
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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