Water → Ethyl {2-[(methylcarbamoyl)amino]-1,3-thiazol-4-yl}acetate

HRID 127113Notes

Reaction equation

HRID 127113 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[CH3:13][N:14]=[C:15]=[O:16].O>CS(C)=O>[CH3:13][NH:14][C:15](=[O:16])[NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12228Methyl IsocyanateHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

Product 1

HCID 20288637Ethyl {2-[(methylcarbamoyl)amino]-1,3-thiazol-4-yl}acetateYield 71.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of ethyl 2-aminothiazol-4-ylacetate (27.4 g.) in dimethylsulfoxide (135 ml.) was dropwise added methylisocyanate (13.05 g.) with stirring at room temperature, and the mixture was stirred for 3 hours at 40° C. After the reaction, the reaction mixture was poured into water (500 ml.), and then extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride in turn and then dried over magnesium sulfate. After distillation of the solvent from the extract, the residue was pulverized in diethyl ether, collected by filtration and then dried to give colorless crystals of ethyl 2-(3-methylureido)thiazol-4-ylacetate (25.7 g.), mp 158° to 159° C.

Workup

  1. stirringthe mixture was stirred for 3 hours at 40° C
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride in turn and then dried over magnesium sulfate
  6. distillationAfter distillation of the solvent from the extract
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-b2b7cf225466449d90456b4cf854b6c7
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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