Water → 2-Chloro-4-phenylthiazole-5-carboxylic acid

HRID 1156604Notes

Reaction equation

HRID 1156604 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:13]([O:15]CC)=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[OH-].[Na+].O>O1CCCC1>[Cl:1][C:2]1[S:3][C:4]([C:13]([OH:15])=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13041816Ethyl 2-chloro-4-phenyl-1,3-thiazole-5-carboxylate

Product 1

HCID 130418282-Chloro-4-phenylthiazole-5-carboxylic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 53.4 g (0.2 mole) of ethyl 2-chloro-4-phenyl-5-thiazolecarboxylate, 8.0 g (0.2 mole) of NaOH, 200 ml. of water and 400 ml. of tetrahydrofuran was stirred for 16 hours and extracted with ether. The organic layer was discarded. The aqueous layer was made acidic and the precipitate was collected and air-dried to give 43.2 g (90%) of the desired product, m.p. 170°-171° C.

Workup

  1. extractionextracted with ether
  2. customthe precipitate was collected
  3. customair-dried

Sources & evidence

ORD record
ord-037f94191c814069bad2c02e159ffa2a
Source dataset
uspto-grants-1982_06
Patent number
US04336389

Reaction notes

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