4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 20288647, compound

HRID 127115Notes

Reaction equation

HRID 127115 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.[Cl:13][C:14]([N:17]=[C:18]=[O:19])([Cl:16])[Cl:15]>C(OCC)(=O)C>[Cl:13][C:14]([Cl:16])([Cl:15])[NH:17][C:18](=[O:19])[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

4

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 580152Trichloromethyl isocyanate2×

Product 1

HCID 20288647HCID 20288647, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-aminothiazol-4-ylacetate (1.86 g.) in dried ethyl acetate (37 ml.) was dropwise added trichloromethylisocyanate (1.6 g.) with stirring under ice-cooling. The mixture was stirred for 2 hours at room temperature, and trichloromethylisocyanate (0.32 g.) was further added thereto, and then the mixture was further stirred for 1 hour at room temperature. After the reaction, the reaction mixture was filtered. The filtrate was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and then the solvent was distilled off therefrom. The residue was pulverized in diethyl ether to give colorless crystals of ethyl 2-(3-trichloromethylureido)thiazol-4-ylacetate (1.72 g.).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. stirringthe mixture was further stirred for 1 hour at room temperature
  4. customAfter the reaction
  5. filtrationthe reaction mixture was filtered
  6. washThe filtrate was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-bc36d5e5a1324e2eb1b4407763b80baf
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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