Pyridine → N-(4-Methylphenyl)benzenesulfonamide

HRID 2350818Notes

Reaction equation

HRID 2350818 reaction equation
C(#N)C.[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.N1C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:18]1([S:24]([NH:4][C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 7369Benzenesulfonyl chlorideHCID 7813p-Toluidine

Product 1

HCID 238717N-(4-Methylphenyl)benzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 ml of an acetonitrile solution containing 32.1 g (0.3 mol) of p-toluidine and 26 ml (0.32 mol) of pyridine was stirred while maintaining it at a temperature of less than 25° C., and 54.7 g (0.31 mol) of benzenesulfonyl chloride was added dropwise thereto. After the addition was completed, the mixture was further stirred for 1 hour and then the reaction solution was added to 1 liter of water. The precipitate formed was extracted with ethyl acetate and then the extract was separated. The ethyl acetate phase was washed with a saline solution and dried over sodium sulfate. The ethyl acetate was distilled off under reduced pressure to yield 74.3 g (0.3 mol) of the desired compound. This compound was used in the subsequent step without purification.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. stirringthe mixture was further stirred for 1 hour
  4. customThe precipitate formed
  5. extractionwas extracted with ethyl acetate
  6. customthe extract was separated
  7. washThe ethyl acetate phase was washed with a saline solution
  8. dry with materialdried over sodium sulfate
  9. distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-90596d4e2ed34ee184b1c403f308f64f
Source dataset
uspto-grants-1989_10
Patent number
USH0000691

Reaction notes

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