Methanol → HCID 58728596, compound

HRID 1992230Notes

Reaction equation

HRID 1992230 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].CO.O>Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]([F:19])([F:17])[F:18])(=[O:14])=[O:15])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 58728461HCID 58728461, compound

Product 1

HCID 58728596HCID 58728596, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl 2-chloro-5-{[(trifluoromethyl)sulfonyl]amino}benzoate (1.0 g, 3.15 mmol), sodium hydroxide (378 mg, 9.44 mmol), methanol (6 ml) and water (6 ml) was stirred for 1 hour. Removal of the volatiles by spin evaporation in vacuo gave a residue that was dissolved in 1 N aqueous hydrochloric acid. The aqueous solution was extracted with ethyl acetate (3 times) and the organic layers were combined, washed with water, and concentrated by spin evaporation in vacuo to give 2-chloro-5-{[(trifluoromethyl)sulfonyl]amino}benzoic acid as a crystalline solid (0.78 g, 82%). 1H-NMR (400 MHz, DMSO-d6): δ 7.63-7.60 (m, 1H), 7.59-7.54 (m, 1H), 7.40-7.35 (m, 1H). ES-LCMS m/z 304 (M+H).

Workup

  1. customRemoval of the volatiles
  2. customby spin evaporation in vacuo
  3. customgave a residue that
  4. extractionThe aqueous solution was extracted with ethyl acetate (3 times)
  5. washwashed with water
  6. concentrationconcentrated by spin evaporation in vacuo

Sources & evidence

ORD record
ord-13a7ec9a203541ddb5edf55cb88478ad
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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