Benzenesulfonamide, N,4-dimethyl- → Phenoxycarbonyl-4-methylbenzene sulfonamide

HRID 860521Notes

Reaction equation

HRID 860521 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].C[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>ClC1C=CC=CC=1Cl>[O:4]([C:2]([C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[S:13]([NH2:12])(=[O:15])=[O:14])=[O:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 15891Phenyl chloroformate

Product 1

HCID 86605513Phenoxycarbonyl-4-methylbenzene sulfonamide

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Phenyl chloroformate (1.57 g, 0.01 mol) and N-methyl-4-methylbenzene sulfonamide (1.85 g, 0.01 mol) were diluted with 1,2-dichlorobenzene (15 ml) and refluxed for 40 hrs. The solvent was evaporated in vacuo and the residue diluted dichloromethane and the dichloromethane washed with water (2×), dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo gave N-methyl-N*-phenoxycarbonyl-4-methylbenzene sulfonamide mp 98–100° C. MS m/z 305. (M+ calcd for C15H15NO4S=305). H NMR (300 MHz, CDCl3) d 2.43 (s, 3, CH3), 2.45 (s, 3, NCH3), 6.95 (m, 2, aromatic), 7.18–7.35 (m, 5, aromatic), 7.88 (m, 5, aromatic).

Workup

  1. temperaturerefluxed for 40 hrs
  2. customThe solvent was evaporated in vacuo
  3. washthe residue diluted dichloromethane and the dichloromethane washed with water (2×)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-53a3180efed34d22a016858e8456da9c
Source dataset
uspto-grants-2006_12
Patent number
US07153925B2

Reaction notes

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