Hydrochloric Acid → 4-Chloro-3-mercapto-2-methylbenzoic acid

HRID 1640386Notes

Reaction equation

HRID 1640386 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH3:14])[C:5]=1[S:15]C(N(C)C)=O.O.Cl>CO>[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:14])[C:5]=1[SH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 86625224Methyl 4-chloro-3-(dimethylaminocarbonylthio)-2-methylbenzoate

Product 1

HCID 667391434-Chloro-3-mercapto-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.61 g (85% by weight pure, 100.1 mmol) of potassium hydroxide were added to 4.80 g (16.7 mmol) of methyl 4-chloro-3-(dimethylaminocarbonylthio)-2-methylbenzoate in 150 ml of methanol, and the mixture was stirred under reflux for two days. The reaction mixture was freed from the solvent, water was added to the residue, the mixture was acidified with 1M HCl and the solid was removed by filtration. This gave 3.2 g of clean product.

Workup

  1. temperatureunder reflux for two days
  2. additionwas added to the residue
  3. customthe solid was removed by filtration

Sources & evidence

ORD record
ord-5b23f01ce6ff480e90f77064a161718a
Source dataset
uspto-grants-2012_02
Patent number
US08114816B2

Reaction notes

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