Chloroacetyl chloride → HCID 86735835, compound

HRID 1981397Notes

Reaction equation

HRID 1981397 reaction equation
Br.[CH2:2]([O:4][N:5]=[C:6]([C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3].[Cl:18]CC(Cl)=O.[C:23]([O:26]CC)(=O)[CH3:24]>CN(C)C(=O)C>[CH2:2]([O:4][N:5]=[C:6]([C:12]1[N:13]=[C:14]([N:17]([Cl:18])[C:23]([CH3:24])=[O:26])[S:15][CH:16]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8857Ethyl AcetateHCID 86735836HCID 86735836, compound

Product 1

HCID 86735835HCID 86735835, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2.43 g of ethyl α-ethoxyimino-2-aminothiazol-4-ylacetate hydrobromide in 25 ml of anhydrous N,N-dimethylacetamide is added 1.43 g of chloroacetyl chloride under cooling and stirring. The solution is stirred for 30 minutes under ice-cooling and then for 30 minutes at room temperature. To the reaction mixture is added 150 ml of ethyl acetate and the mixture is repeatedly washed with saturated aq. NaCl solution. The ethyl acetate layer is dried over anhydrous magnesium sulfate, and subjected to the distillation of the solvent under reduced pressure. To the residue is added water to precipitate solid material. The solid is collected by filtration and dried. The procedure gives 1.90 g of ethyl α-ethoxyimino-2-(chloroacetamino)thiazol-4-ylacetate. Yield 79%.

Workup

  1. temperatureunder cooling
  2. stirringThe solution is stirred for 30 minutes under ice-
  3. temperaturecooling
  4. washthe mixture is repeatedly washed with saturated aq. NaCl solution
  5. dry with materialThe ethyl acetate layer is dried over anhydrous magnesium sulfate
  6. distillationsubjected to the distillation of the solvent under reduced pressure
  7. additionTo the residue is added water
  8. customto precipitate solid material
  9. filtrationThe solid is collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-a829d4b42c6343ab80a3331fa5731b19
Source dataset
uspto-grants-1985_04
Patent number
US04514565

Reaction notes

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