Methylamine → 2-Chloro-4-fluoro-5-[(methylamino)sulfonyl]benzoic acid

HRID 1992145

Reaction equation

HRID 1992145 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:16][NH2:17]>>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([S:12]([NH:17][CH3:16])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 45719302-Chloro-5-chlorosulfonyl-4-fluorobenzoic acid

Product 1

HCID 587282922-Chloro-4-fluoro-5-[(methylamino)sulfonyl]benzoic acid

Procedure

At 0° C., to a stirred ice-water suspension (˜200 mL) of 2-chloro-5-(chlorosulfonyl)-4-fluorobenzoic acid was slowly added a precooled 40% methylamine (13 mL). The reaction mixture was then stirred for 2 hours before being acidified to pH˜2. The desired product was precipitated and filtered out. After being dried overnight, the pure 2-chloro-4-fluoro-5-[(methylamino)sulfonyl]benzoic acid was obtained as white solid (9.8 g, 100%).

Workup

  1. customThe desired product was precipitated
  2. filtrationfiltered out
  3. customAfter being dried overnight

Sources & evidence

ORD record
ord-d4cdc502fd844cb393bdfcf4550de3ac
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Linked notes

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