Chloroacetonitrile → ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(cyanomethoxyimino)acetate

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Reaction Steps

54 g of ethyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate are dissolved in 500 ml of dimethylformamide. After the addition of 138 g of potassium carbonate, there are added dropwise within 1 hour 47 ml of chloroacetonitrile and the mixture is then stirred at room temperature for 20 hours. The dark solution obtained is poured into ice-water and extracted with ethyl acetate. The organic phase is washed with water, treated with active carbon, dried over magnesium sulphate and concentrated. After recrystallization from toluene, there are obtained 38 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetate of melting point 167°-168° C.

Provenance & Evidence