Potassium Hydroxide → HCID 67766715, compound

HRID 223630Notes

Reaction equation

HRID 223630 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([NH:16][C:17](=[O:20])[CH2:18][Cl:19])[N:6]([C:11]1[N:12]=[CH:13][S:14][CH:15]=1)[C:7](=[O:10])[CH2:8][Cl:9])C.[OH-].[K+]>C(O)C.O>[Cl:19][CH2:18][C:17]([NH:16][CH:5]([C:4]([OH:21])=[O:3])[N:6]([C:11]1[N:12]=[CH:13][S:14][CH:15]=1)[C:7](=[O:10])[CH2:8][Cl:9])=[O:20]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67766678HCID 67766678, compound

Product 1

HCID 67766715HCID 67766715, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.54 g of 2-chloroacetamidothiazol-4-yl N-chloroacetylglycine ethyl ester in 30 ml of ethanol is added dropwise a solution of 1.68 g of potassium hydroxide in 15 ml of water under ice-cooling, followed by the stirring for 15 minutes. Ethanol is distilled under reduced pressure and the residue is made acidic with 10% hydrochloric acid, followed by the extraction with ethyl acetate. The ethyl acetate layer is washed with water and dried. The distillation of ethyl acetate gives 2.38 g of 2-chloroacetamidothiazol-4-yl N-chloroacetylglycine as colorless crystals. Melting point: 184°-186° C.

Workup

  1. temperaturecooling
  2. customstirring for 15 minutes
  3. distillationEthanol is distilled under reduced pressure
  4. extractionfollowed by the extraction with ethyl acetate
  5. washThe ethyl acetate layer is washed with water
  6. customdried
  7. distillationThe distillation of ethyl acetate

Sources & evidence

ORD record
ord-6d8b824ceb944911b4c3fa311c349c79
Source dataset
uspto-grants-1982_10
Patent number
US04355160

Reaction notes

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