Hydroxide → 5-Thiazolecarboxylic acid, 2-(hydroxymethyl)- (9CI)

HRID 1414588Notes

Reaction equation

HRID 1414588 reaction equation
C([O:9][CH2:10][C:11]1[S:12][C:13]([C:16]([O:18]CC)=[O:17])=[CH:14][N:15]=1)(=O)C1C=CC=CC=1.[OH-]>O>[OH:9][CH2:10][C:11]1[S:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 961HydroxideHCID 21488109HCID 21488109, compound

Product 1

HCID 220252925-Thiazolecarboxylic acid, 2-(hydroxymethyl)- (9CI)Yield 68.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 13.5 g of ethyl 2-benzoyloxymethyl-thiazole-5-carboxylate, 135 ml of water and 8 ml of postassium hydroxide was heated at 95° C with stirring for an hour and the mixture was cooled and extracted with ether. The aqueous phase was acidified and was then saturated with sodium chloride. The mixture was extracted with ethyl acetate and the organic extracts were washed with water, dried and evaporated to dryness to obtain 11,5 g of raw product. The product was chromatographed over silica gel and was eluted with a 8-2 methylene chloride-ethanol mixture containing 2% acetic acid. The 6 g of product were crystallized from a 3-1 acetone-methanol mixture to obtain 5.04 g of 2-hydroxymethyl-thiazole -5-carboxylic acid melting at 193° C.

Workup

  1. temperaturethe mixture was cooled
  2. extractionextracted with ether
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic extracts were washed with water
  5. customdried
  6. customevaporated to dryness
  7. customto obtain 11,5 g of raw product
  8. customThe product was chromatographed over silica gel
  9. washwas eluted with a 8-2 methylene chloride-ethanol mixture
  10. additioncontaining 2% acetic acid
  11. customThe 6 g of product were crystallized from a 3-1 acetone-methanol mixture

Sources & evidence

ORD record
ord-24ead66d964148d5b9a3cade2332788c
Source dataset
uspto-grants-1977_01
Patent number
US04001447

Reaction notes

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