Ammonium Hydroxide → N-(5-Fluoro-2-methyl-4-sulfamoylphenyl)acetamide

HRID 1106230Notes

Reaction equation

HRID 1106230 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:7][C:6]=1[CH3:16])(=[O:3])[CH3:2].[OH-].[NH4+:18]>>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([S:12](=[O:14])(=[O:13])[NH2:18])=[CH:7][C:6]=1[CH3:16])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 20553703HCID 20553703, compound

Product 1

HCID 20553706N-(5-Fluoro-2-methyl-4-sulfamoylphenyl)acetamide

Procedure

The moist 2-acetamido-4-fluoro-5-chlorosulphonyltoluene (3) was heated in 650 ml of concentrated ammonium hydroxide until it reached 50°. The resulting solution was cooled and extracted with ethyl acetate, (10×1000 ml). The extracts were combined and concentrated in vacuo, to give a solid. The latter was purified by dissolving the solid in 350 ml of a 20% aqueous solution of sodium hydroxide, filtering this mixture and acidifying the filtrate with concentrated hydrochloric acid. The precipitate, which separated out, was recovered, then dried; yield: 32.9 g (23.4%); m.p.: 205-207°; literature:1 m.p.: 206-208°.

Workup

  1. customreached 50°
  2. temperatureThe resulting solution was cooled
  3. extractionextracted with ethyl acetate, (10×1000 ml)
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customThe latter was purified
  7. dissolutionby dissolving the solid in 350 ml of a 20% aqueous solution of sodium hydroxide
  8. filtrationfiltering this mixture
  9. customThe precipitate, which separated out
  10. customwas recovered
  11. customdried
  12. custom206-208°

Sources & evidence

ORD record
ord-bd463f940cf547ec9ab26dabb967e686
Source dataset
uspto-grants-1982_01
Patent number
US04312862

Reaction notes

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