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

HRID 548589Notes

Reaction equation

HRID 548589 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 (purity 85% by weight, 100.1 mmol) of KOH 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 solvent, water was added to the residue, which was then acidified with 1M HCl, and the solid was collected by filtration. This gave 3.2 g of pure product.

Workup

  1. temperatureunder reflux for two days
  2. additionwas added to the residue, which
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-aa83821db1ab4b92898a4d5ba1be772c
Source dataset
uspto-grants-2011_05
Patent number
US07943551B2

Reaction notes

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