Sodium Bicarbonate → Ethyl [2-(carbamoylamino)-1,3-thiazol-4-yl]acetate

HRID 127116Notes

Reaction equation

HRID 127116 reaction equation
ClC(Cl)(Cl)[NH:3][C:4](=[O:17])[NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:10]=1.C(=O)(O)[O-].[Na+]>CO.O>[NH:5]([C:6]1[S:7][CH:8]=[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:10]=1)[C:4]([NH2:3])=[O:17]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 20288647HCID 20288647, compound

Product 1

HCID 20288653Ethyl [2-(carbamoylamino)-1,3-thiazol-4-yl]acetateYield 82.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 2-(3-trichloromethylureido)thiazol-4-ylacetate (6.32 g.) in a mixture of methanol (400 ml.) and water (150 ml.) was adjusted to pH 7 to 7.6 with sodium bicarbonate aqueous solution with stirring at room temperature, and then the solution was stirred for 70 minutes at the same temperature. The methanol was distilled off from the reaction mixture under reduced pressure, and the precipitates were collected by filtration, washed with water and then dried to give colorless crystals of ethyl 2-ureidothiazol-4-ylacetate (3.45 g.), mp 173° to 174° C.

Workup

  1. stirringthe solution was stirred for 70 minutes at the same temperature
  2. distillationThe methanol was distilled off from the reaction mixture under reduced pressure
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-cfb46f823d0c4d6b831ccefdc84ea38d
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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