Ammonia → 4-Fluorobenzenesulfonamide

HRID 2300969Notes

Reaction equation

HRID 2300969 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH3:12]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 1202314-Fluorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorobenzenesulfonylchloride (25 g) were dissolved in dichloromethane (250 ml) and treated at 0° C. with an aqueous solution of ammonia (25%, 50 ml). The mixture was stirred for 2 hours with cooling and overnight at room temperature. The reaction mixture was acidified and the organic solvent evaporated. The residue was extracted with ethyl acetate to yield 20 g 4-fluorobenzenesulfonamide, which were dissolved in water (300 ml), treated with 1-benzyl-piperazine (102 g) and refluxed for 24 hours. The reaction mixture was filtered to yield 26 g of the title compound. (mass spec APCI [M+H]=332)

Workup

  1. customthe organic solvent evaporated
  2. extractionThe residue was extracted with ethyl acetate

Sources & evidence

ORD record
ord-4e646276ff564fab92ef4a0bc635cc83
Source dataset
uspto-grants-2002_12
Patent number
US06498252B1

Reaction notes

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