Hydrochloric Acid → HCID 22621135, compound

HRID 2393006Notes

Reaction equation

HRID 2393006 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:5]=1.Cl>CO>[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:16])=[O:17])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22621194HCID 22621194, compound

Product 1

HCID 22621135HCID 22621135, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N Sodium hydroxide solution (20 ml) was added to a stirred solution of methyl 4-chloro-2-(N-methyl-N-methylsulphonylamino)benzoate (2.75 g) in methanol. The mixture was stirred at reflux for 0.5 hours. After cooling, the mixture was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic extracts were combined, dried and evaporated to yield 4-chloro-2-(N-methyl-N-methylsulphonylamino)benzoic acid as a white solid (2.45 g), m.p. 161°-164° C.

Workup

  1. temperatureat reflux for 0.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-44b1124f55d64cb7869c9360938dc857
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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