Water → n-(4-Cyanophenyl)-4-methylbenzenesulfonamide

HRID 1356664Notes

Reaction equation

HRID 1356664 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.O>N1C=CC=CC=1.C(#N)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 133964-Aminobenzonitrile

Product 1

HCID 257975n-(4-Cyanophenyl)-4-methylbenzenesulfonamideYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

4-Aminobenzonitrile (98%, 500.0 g (4.15 mol) was dissolved in a mixed solvent of pyridine (360 ml) and acetonitrile (900 ml). To this, p-toluenesulfonyl chloride (872.3 g (4.44 mol)) was added with stirring at room temperature. After stirring for 16 hours at room temperature, water (4000 ml) was added to the reaction mixture to bring about separation of crystals. The crystals were filtered and washed with water to give 1153 g (98%) of 4′-cyano-p-toluenesulfonanilide as pale red crude crystals.

Workup

  1. stirringAfter stirring for 16 hours at room temperature
  2. customto bring about separation of crystals
  3. filtrationThe crystals were filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-fe1a1a27fabb4a81bff7de403bc264c5
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

Loading…