Methanol → HCID 58727963, compound

HRID 1992233Notes

Reaction equation

HRID 1992233 reaction equation
[F:1][C:2]([F:26])([F:25])[S:3]([N:6](S(C(F)(F)F)(=O)=O)[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[C:9]([Cl:17])[CH:8]=1)(=[O:5])=[O:4].[OH-].[Na+].CO.O>Cl>[Cl:17][C:9]1[CH:8]=[C:7]([NH:6][S:3]([C:2]([F:26])([F:1])[F:25])(=[O:4])=[O:5])[CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 58727961HCID 58727961, compound

Product 1

HCID 58727963HCID 58727963, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl 4-{bis[(trifluoromethyl)sulfonyl]amino}-2-chlorobenzoate (5.9 g, 13.1 mmol), sodium hydroxide (3.12 g, 78.0 mmol), methanol (125 ml) and water (125 ml) was stirred for 2 hours. The solution from concentration to 75 ml by spin evaporation in vacuo and dilution with 100 ml water was extracted with ethyl acetate. The aqueous layer was acidified with 12 N hydrochloric acid and again extracted with ethyl acetate. The organic layer was washed with water and concentrated by spin evaporation in vacuo, with the addition of dichloromethane (3 times) to give 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 2-chloro-4-{[(trifluoromethyl)sulfonyl]amino}benzoic acid as a solid (3.6 g, 61%). ES-LCMS m/z 304 (M+H).

Workup

  1. concentrationThe solution from concentration to 75 ml
  2. customby spin evaporation in vacuo and dilution with 100 ml water
  3. extractionwas extracted with ethyl acetate
  4. extractionagain extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. concentrationconcentrated by spin evaporation in vacuo, with the addition of dichloromethane (3 times)
  7. customto give a residue that
  8. extractionThe aqueous solution was extracted with ethyl acetate (3 times)
  9. washwashed with water
  10. concentrationconcentrated by spin evaporation in vacuo 2-chloro-4-{[(trifluoromethyl)sulfonyl]amino}benzoic acid as a solid (3.6 g, 61%)

Sources & evidence

ORD record
ord-8f53fb5c232f436bb489d2ebc36dfbfd
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…