Water → 4-{[(4-Methylphenyl)sulfonyl]amino}phenyl thiocyanate

HRID 1356672

Reaction equation

HRID 1356672 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.O>N1C=CC=CC=1>[S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[CH:3][CH:4]=1)[C:9]#[N:10]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 76336[(4-Aminophenyl)sulfanyl]formonitrile

Product 1

HCID 8034834-{[(4-Methylphenyl)sulfonyl]amino}phenyl thiocyanateYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-Aminophenyl thiocyanate (10.0 g (66.6 mmol)) in pyridine (70 ml), p-toluenesulfonyl chloride (12.7 g (66.6 mmol)) was added with stirring at room temperature, and the mixture was stirred at room temperature for 16 hours. Then, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 19.4 g (98%) of 4′-thiocyano-p-toluenesulfonanilide as pale yellow crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with dilute hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2506627016cf4c9f849692e0a60c3e4b
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Linked notes

Loading…