Ammonia → 5-Acetyl-2-fluorobenzenesulphonamide

HRID 461209Notes

Reaction equation

HRID 461209 reaction equation
[NH2:1]C1C=C(C(=O)C)C=CC=1F.N([O-])=O.[Na+].S(=O)(O)[O-].[Na+].Cl[S:22]([C:25]1[CH:26]=[C:27]([C:32](=[O:34])[CH3:33])[CH:28]=[CH:29][C:30]=1[F:31])(=[O:24])=[O:23].N>Cl.O.C(O)(=O)C>[F:31][C:30]1[CH:29]=[CH:28][C:27]([C:32](=[O:34])[CH3:33])=[CH:26][C:25]=1[S:22](=[O:24])(=[O:23])[NH2:1]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 106069533'-Amino-4'-fluoroacetophenoneHCID 227604443'-Chlorosulfonyl-4'-fluoroacetophenoneHCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Product 1

HCID 213316525-Acetyl-2-fluorobenzenesulphonamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Procedure

4.9 g of 3'-amino-4'-fluoroacetophenone were diazotized in 25 ml of concentrated hydrochloric acid at 0° to 5° C with a solution of 2.3 g of NaNO2 in 5 ml of water and treated with a solution, prepared from 2.7 g of sodium bisulfite in 5 ml of water and 25 ml of concentrated hydrochloric acid and the oily 3'-chlorosulfonyl-4'-fluoroacetophenone was reacted with 20 ml of liquid ammonia to give the 4'-fluoro-3'-sulfamoylacetophenone, melting point: 135° C from glacial acetic acid.

Workup

  1. additiontreated with a solution

Sources & evidence

ORD record
ord-34cff539a78e42fdb79bffeeac786317
Source dataset
uspto-grants-1977_12
Patent number
US04061761

Reaction notes

Loading…