Chloroacetyl chloride → Ethyl alpha-methoxyimino-alpha-[2-(chloroacetamido)thiazol-4-yl]acetate

HRID 1154878Notes

Reaction equation

HRID 1154878 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:16][CH2:17][C:18](Cl)=[O:19]>CC(N(C)C)=O>[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:11]=[C:12]([NH:15][C:18](=[O:19])[CH2:17][Cl:16])[S:13][CH:14]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

Product 1

HCID 3593442Ethyl alpha-methoxyimino-alpha-[2-(chloroacetamido)thiazol-4-yl]acetateYield 94.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 10 g of ethyl α-methoxyimino-α-(2-aminothiazol-4-yl)acetate in 100 ml of dimethylacetamide is dropwise added 5.91 g of chloroacetyl chloride under ice-cooling. After the stirring for 1 hour at room temperature, the reaction mixture is poured into ice-water and the resultant solution is extracted with ethyl acetate. The organic layer is washed and dried, followed by the distillation of solvent to give 12.66 g of ethyl α-methoxyimino-α-[2-(chloroacetamido)thiazol-4-yl]acetate as a crystal. Melting point: 81°-82° C.

Workup

  1. temperaturecooling
  2. extractionthe resultant solution is extracted with ethyl acetate
  3. washThe organic layer is washed
  4. customdried
  5. distillationfollowed by the distillation of solvent

Sources & evidence

ORD record
ord-53e99ac9a354444287c405d27dfbdcb5
Source dataset
uspto-grants-1981_11
Patent number
US04298606

Reaction notes

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