Benzenesulfonamide, N,4-dimethyl- → 2,4-Dimethylbenzenesulfonamide

HRID 860519Notes

Reaction equation

HRID 860519 reaction equation
C[NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH3:13]C1C=CC(C(Cl)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:13][C:7]1[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:6]=1[S:3]([NH2:2])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 134054-Methylbenzoyl Chloride

Product 1

HCID 819742,4-Dimethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-Methyl-4-methylbenzene sulfonamide (3.70 g, 0.02 mol) and 4-methylbenzoyl chloride (3.08 g, 0.02 mol) were dissolved in xylene and refluxed for 72 hrs. After evaporation of the xylene, the residue was dissolved in ethyl acetate and washed with dilute sodium carbonate solution. After separation, drying over anhydrous magnesium sulfate and evaporation of the solvent in vacuo, the residue was recrystallized from hexane-ethyl acetate to give N-4-methylbenzoyl-N*-methyl-4-methylbenzene sulfonamide mp 90–92° C. MS m/z 303. (M+ calcd for C16H17NO3S=303). H NMR (300 Mhz, CDCl3) d 2.30 (s, 3, CH3), 2.46 (s, 3, CH3), 7.21 (m, 2, aromatic), 7.35 (m, 2, aromatic), 7.49 (m, 2, aromatic), 7.84 (m, 2, aromatic).

Workup

  1. temperaturerefluxed for 72 hrs
  2. customAfter evaporation of the xylene
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with dilute sodium carbonate solution
  5. customAfter separation
  6. dry with materialdrying over anhydrous magnesium sulfate and evaporation of the solvent in vacuo
  7. customthe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-b34ae788ecda4525817bb2373884b1d5
Source dataset
uspto-grants-2006_12
Patent number
US07153925B2

Reaction notes

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