Potassium Hydroxide → 5-Methyl-2-(5-methyl-2-thienyl)-4-thiazolecarboxylic acid

HRID 1638318Notes

Reaction equation

HRID 1638318 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([CH3:17])=[C:10]([C:12]([O:14]CC)=[O:13])[N:11]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH3:1][C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([CH3:17])=[C:10]([C:12]([OH:14])=[O:13])[N:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19842275HCID 19842275, compound

Product 1

HCID 156230735-Methyl-2-(5-methyl-2-thienyl)-4-thiazolecarboxylic acidYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-(5-methyl-2-thienyl)-5-methyl-4-thiazolecarboxylate (1.47 g) in methanol (100 ml) was added 1N aqueous potassium hydroxide (16.5 ml) and the mixture was heated at 60° C. for 40 minutes. Then the solvent was removed from the reaction mixture. The residue was treated with water and acidified with 2N hydrochloric acid under ice-cooling. The deposited solids were filtered and washed with water, recrystallized from methanol-water to give yellowish crystals of 2-(5-methyl-2-thienyl)-5-methyl-4-thiazolecarboxylic acid (1.06 g, yield 80%), m.p. 160°-161° C.

Workup

  1. customThen the solvent was removed from the reaction mixture
  2. additionThe residue was treated with water
  3. temperaturecooling
  4. filtrationThe deposited solids were filtered
  5. washwashed with water
  6. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-17291719ace645a9b7ffba49c911a41f
Source dataset
uspto-grants-1989_11
Patent number
US04879295

Reaction notes

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