N,N-Dimethylaniline → HCID 70582645, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 0.625 g of powdered phosphorous pentachloride in 20 ml of dichloromethane is added 0.474 g of pyridine under stirring at -40° C. To the resulting mixture is added dropwise a solution of 0.422 g of 7-thienylacetamido-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylic acid (obtained in Example 42) in 10 ml of dichloromethane, 0.242 g of dimethylaniline and then 0.3 ml of dimethyldichlorosilane under stirring at -40° C. After stirring for 30 minutes at 0° C., to the reaction mixture is added 5 ml of methanol under stirring at -40° C., and the mixture is poured into cold water. The aqueous layer is neutralized to pH 5.5 with an aqueous solution of sodium bicarbonate and washed three times with dichloromethane. The solution is charged on a column of Amberlite XAD-II and eluted with water. The fractions containing the desired product are collected and lyophilized to give 0.140 g of 7-amino-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylic acid.

Provenance & Evidence