Potassium Hydroxide → {2-[(Methylcarbamoyl)amino]-1,3-thiazol-4-yl}acetic acid

HRID 127114Notes

Reaction equation

HRID 127114 reaction equation
[CH3:1][NH:2][C:3](=[O:16])[NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][C:11]([O:13]CC)=[O:12])[N:9]=1.[OH-].[K+]>CO.O>[CH3:1][NH:2][C:3](=[O:16])[NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][C:11]([OH:13])=[O:12])[N:9]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20288637Ethyl {2-[(methylcarbamoyl)amino]-1,3-thiazol-4-yl}acetate

Product 1

HCID 20288645{2-[(Methylcarbamoyl)amino]-1,3-thiazol-4-yl}acetic acidYield 85.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(3-methylureido)thiazol-4-ylacetate (12.8 g.) in a mixture of methanol (240 ml.) and water (240 ml.) was dropwise added 1 N potassium hydroxide aqueous solution (52.7 ml.) with stirring at room temperature, and the solution was stirred for overnight at the same temperature, and then methanol was distilled off therefrom under reduced pressure. The remaining aqueous layer was washed with ethyl acetate, and then 1 N hydrochloric acid (52.7 ml.) was added thereto under ice-cooling. The precipitated crystals were collected by filtration, washed with water and then dried to give colorless crystals of 2-(3-methylureido)thiazol-4-ylacetic acid (9.7 g.), mp 190° C. (dec.).

Workup

  1. stirringthe solution was stirred for overnight at the same temperature
  2. distillationmethanol was distilled off
  3. washThe remaining aqueous layer was washed with ethyl acetate
  4. addition1 N hydrochloric acid (52.7 ml.) was added
  5. temperatureunder ice-cooling
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-7a0f1198a66b4233988745ff78fc7b87
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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