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

HRID 223625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 223625
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 3593442Ethyl alpha-methoxyimino-alpha-[2-(chloroacetamido)thiazol-4-yl]acetateAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-40696b2f3ab74a3196df4c49ed91eaa8
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04355160

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