Ammonium Hydroxide → 5-fluoro-2-methylbenzenesulfonamide

HRID 1372236Notes

Reaction equation

HRID 1372236 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[NH4+:13].[OH-]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8]([NH2:13])(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1362865-Fluoro-2-methylbenzenesulphonyl chloride

Product 1

HCID 3410785-fluoro-2-methylbenzenesulfonamideYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-fluoro-2-methyl-benzenesulfonyl chloride (4.18 g, 20 mmol) in acetone (20 mL) was added, dropwise, concentrated NH4OH (3 mL) and the resulting mixture stirred for 5 min. Acetone was removed in vacuo and the precipitates were filtered, washed thoroughly with water and dried in vacuo to provide 3.7 g (Yield 98%) of the title compound as a white solid; 1H NMR (500 MHz, DMSO-D6) δ ppm: 2.55 (3H, s) 7.33–7.40 (1H, m) 7.40–7.46 (1H, m) 7.54 (2H, s) 7.59 (1H, dd, J=9.2, 2.7 Hz); LC/MS m/z 190 (M+H).

Workup

  1. customAcetone was removed in vacuo
  2. filtrationthe precipitates were filtered
  3. washwashed thoroughly with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e643454e786d4483b4e21cebfb02d54c
Source dataset
uspto-grants-2007_01
Patent number
US07157447B2

Reaction notes

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