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

HRID 1992132

Reaction equation

HRID 1992132 reaction equation
Cl[C:2]1[C:10]([S:11](Cl)(=[O:13])=[O:12])=[C:9]([F:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:16][NH2:17].[ClH:18]>O>[Cl:18][C:7]1[CH:8]=[C:9]([F:15])[C:10]([S:11]([NH:17][CH3:16])(=[O:13])=[O:12])=[CH:2][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 866084732-Chloro-3-chlorosulfonyl-4-fluorobenzoic acid

Product 1

HCID 587282922-Chloro-4-fluoro-5-[(methylamino)sulfonyl]benzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.02 g (73.4 mmol) of 2-chloro-3-chlorosulfonyl-4-fluorobenzoic acid was added as a solid to a cooled solution of 10.5 mL of methylamine (40% aqueous solution, 293.6 mmol) in 400 mL of water. Reaction was monitored by LC/MS and complete after one hour. The reaction was acidified to pH=1 with concentrated HCl, and solid precipitated out. Product was obtained by filtration. 17.54 g obtained as a pale tan solid (89% yield). 1H NMR (300 MHz, DMSO-d6) δ13.83-14.01 (br, 1H), 8.21-8.26 (d, 1H, J=9.11 Hz), 7.98-8.03 (q, 1H, J=4.82), 7.88-7.92 (d, 1H, J=9.11 Hz), 2.55-2.56 (d, 3H, J=4.82 Hz).

Workup

  1. customReaction
  2. customprecipitated out
  3. customProduct was obtained by filtration

Sources & evidence

ORD record
ord-8a06829d0b7b48edb77db886836d0741
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Linked notes

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