Water → Benzenesulfonamide, N-(4-chlorophenyl)-4-methyl-

HRID 1356658Notes

Reaction equation

HRID 1356658 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.O>N1C=CC=CC=1.C(#N)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 78124-Chloroaniline

Product 1

HCID 76182Benzenesulfonamide, N-(4-chlorophenyl)-4-methyl-Yield 102%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloroaniline (98%, 500 g (3.84 mol) in pyridine (338 ml) and acetonitrile (800 ml), p-toluenesulfonyl chloride (807.8 g (4.11 mol)) was added with stirring at temperature below 15° C. After stirring for 16 hours at room temperature, water (4000 ml) was added to the reaction mixture and stirring was continued for 3 hours to have crystals separated. The crystals were then filtered and washed with water to give 1100 g (102%) of 4′-chloro-p-toluenesulfonanilide as pale red crude crystals.

Workup

  1. stirringAfter stirring for 16 hours at room temperature
  2. stirringstirring
  3. customseparated
  4. filtrationThe crystals were then filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-6fa1596b00844a6ab26db76c2c6116dd
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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