Potassium Hydroxide → [2-(Carbamoylamino)-1,3-thiazol-4-yl]acetic acid

HRID 127117Notes

Reaction equation

HRID 127117 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][C:11]([O:13]CC)=[O:12])[N:9]=1)[C:2]([NH2:4])=[O:3].[OH-].[K+]>CO.O>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][C:11]([OH:13])=[O:12])[N:9]=1)[C:2]([NH2:4])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20288653Ethyl [2-(carbamoylamino)-1,3-thiazol-4-yl]acetate

Product 1

HCID 16785394[2-(Carbamoylamino)-1,3-thiazol-4-yl]acetic acidYield 89.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-ureidothiazol-4-ylacetate (3.1 g.) in a mixture of methanol (62 ml.) and water (41 ml.) was dropwise added 1 N potassium hydroxide aqueous solution (13.6 ml) with stirring under ice-cooling, and the solution was stirred for overnight at room temperature, and then the solvent was distilled off therefrom. The residue was dissolved in water (150 ml.), washed with ethyl acetate and then adjusted to pH 3.5 with 10% hydrochloric acid. Thus obtained aqueous layer was cooled with ice, and the precipitates were collected by filtration, washed with cold water (10 ml.) and then dried to give colorless crystals of 2-ureidothiazol-4-ylacetic acid (2.44 g.), mp 189° C. (dec.).

Workup

  1. temperaturecooling
  2. stirringthe solution was stirred for overnight at room temperature
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in water (150 ml.)
  5. washwashed with ethyl acetate
  6. temperatureThus obtained aqueous layer was cooled with ice
  7. filtrationthe precipitates were collected by filtration
  8. washwashed with cold water (10 ml.)
  9. customdried

Sources & evidence

ORD record
ord-c9d1f203fdd6451ea87f90eadc2b9a78
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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