Potassium Hydroxide → 2-Propyl-5-thiazole-acetic acid

HRID 972836Notes

Reaction equation

HRID 972836 reaction equation
[CH2:1]([C:4]1[S:5][C:6]([CH2:9][C:10]([O:12]CC)=[O:11])=[CH:7][N:8]=1)[CH2:2][CH3:3].[OH-].[K+]>CO>[CH2:1]([C:4]1[S:5][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][N:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54320013Ethyl (2-propyl-1,3-thiazol-5-yl)acetate

Product 1

HCID 214055832-Propyl-5-thiazole-acetic acidYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.13 g of ethyl 2-propyl-5-thiazole acetate, 11 ml of methanol and 1.1 ml of potassium hydroxide was stirred for 1 hour under a nitrogen atmosphere at room temperature and the methanol was distilled under reduced pressure. The residue was dissolved in 5 ml of water and 2 ml of concentrated hydrochloric acid and then 2.1 g of sodium acetate were added thereto. The mixture was extracted with methylene chloride and the organic extracts were dried and evaporated to dryness. The residue was crystallized from toluene to obtain 1.24g of 2-propyl-5-thiazole-acetic acid melting at 95° C.

Workup

  1. distillationthe methanol was distilled under reduced pressure
  2. dissolutionThe residue was dissolved in 5 ml of water
  3. addition2 ml of concentrated hydrochloric acid and then 2.1 g of sodium acetate were added
  4. extractionThe mixture was extracted with methylene chloride
  5. customthe organic extracts were dried
  6. customevaporated to dryness
  7. customThe residue was crystallized from toluene

Sources & evidence

ORD record
ord-2648237ccd9e4539a84c3db7c59c2720
Source dataset
uspto-grants-1977_10
Patent number
US04053618

Reaction notes

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