Thiourea → HCID 13826570, compound

Participants

Reaction Steps

A solution of 35.2 g of allyl 4-chloro-acetoacetate in 34 ml of acetic acid is treated dropwise within 45 minutes while stirring and cooling with a solution of 14.6 g of sodium nitrite in 21 ml of water. During the addition the temperature falls gradually from 0° C. to -15° C. The mixture is subsequently stirred at -15° C. for 2 hours. A solution of 15.2 g of thiourea in 120 ml of water, pre-warmed to 30° C., is treated with the resulting solution at such a rate that the temperature remains at about 30°-35° C. After stirring for an additional 7 hours, the crystalline precipitate obtained is filtered off, washed successively with water, acetonitrile and ether and crystallized from acetonitrile. There are obtained 21.8 g (48%) of allyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate of melting point 184°-185° C.

Provenance & Evidence