Potassium Hydroxide → 2-p-Chlorophenyl-5-phenylthio-4-thiazoleacetic acid

HRID 46770Notes

Reaction equation

HRID 46770 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([S:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:11]([CH2:13][C:14]([O:16]CC)=[O:15])[N:12]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([S:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54037631Ethyl 2-p-chlorophenyl-5-phenylthio-4-thiazoleacetate

Product 1

HCID 541246842-p-Chlorophenyl-5-phenylthio-4-thiazoleacetic acidYield 72.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.4 g of ethyl 2-p-chlorophenyl-5-phenylthio-4-thiazoleacetate in 100 ml of methanol was added 15 ml of 3 N aqueous potassium hydroxide. The mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure and water was added to the residue. The solution was acidified with hydrochloric acid. The white precipitated solid was filtered off, washed with water, dried and recrystallized from ethanol to give 2.3 g of the title compound, melting at 191°-193° C.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added to the residue
  3. customThe white precipitated solid
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7d4bf85428134dbaa864623b14535ef5
Source dataset
uspto-grants-1979_11
Patent number
US04175130

Reaction notes

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