Water → p-Toluenesulfonanilide, 4'-fluoro-

HRID 1356661Notes

Reaction equation

HRID 1356661 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>C(#N)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 97314-Fluoroaniline

Product 1

HCID 853960p-Toluenesulfonanilide, 4'-fluoro-Yield 102%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-fluoroaniline (200.0 g (1.80 mol) in pyridine (155.0 g (1.96 mol)) and acetonitrile (155 ml), under cooling with ice and with stirring, p-toluenesulfonyl chloride (360.3 g (1.89 mol)) was added. After stirring for 20 hours at room temperature, water (1500 ml) was added to the reaction mixture to bring about separation of crystals. The crystals were filtered and washed with water to give 486.6 g (102%) of 4′-fluoro-p-toluenesulfonanilide as pale red crude crystals.

Workup

  1. stirringAfter stirring for 20 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-921da409f4ca46b8a77484638ca34720
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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