Hydrochloric Acid → HCID 22621135, compound

HRID 430427Notes

Reaction equation

HRID 430427 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-17aee627e02d4fbba0f4b27ad9ffc2f3
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

Loading…