Potassium Hydroxide → 2-(Methoxymethyl)-4-methyl-1,3-thiazole-5-carboxylic acid

HRID 275352Notes

Reaction equation

HRID 275352 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[S:12][C:11]([CH2:13][O:14][CH3:15])=[N:10][C:9]=1[CH3:16])=[O:7])C>C(O)C>[CH3:15][O:14][CH2:13][C:11]1[S:12][C:8]([C:6]([OH:7])=[O:5])=[C:9]([CH3:16])[N:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 53930828HCID 53930828, compound

Product 1

HCID 200880752-(Methoxymethyl)-4-methyl-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.7 g of 85% potassium hydroxide in 1130 ml of ethanol are added at room temperature to 22.1 g of 2-methoxymethyl-4-methylthiazole-5-carboxylic acid ethyl ester and the reaction mixture is then heated under reflux for 18 hours. After cooling, the ethanol is evaporated off and the residue is dissolved in 200 ml of water. After stirring with active carbon, the mixture is filtered over Hyflo and the filtrate is acidified with concentrated hydrochloric acid with vigorous stirring. The resulting yellowish crystals are filtered off, washed with water and dried. After recrystallisation from tetrahydrofuran/petroleum ether (30°-45° C.) (=10:1) the yellowish crystals melt at 168°-169.5° C.

Workup

  1. temperaturethe reaction mixture is then heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. customthe ethanol is evaporated off
  5. dissolutionthe residue is dissolved in 200 ml of water
  6. filtrationthe mixture is filtered over Hyflo
  7. filtrationThe resulting yellowish crystals are filtered off
  8. washwashed with water
  9. customdried
  10. customAfter recrystallisation from tetrahydrofuran/petroleum ether (30°-45° C.) (=10:1) the yellowish crystals
  11. custommelt at 168°-169.5° C.

Sources & evidence

ORD record
ord-4b748890776d4c28a94c5b6594464130
Source dataset
uspto-grants-1995_02
Patent number
US05393766

Reaction notes

Loading…