Malononitrile → (+)-[[4-(3,6-dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)phenyl]hydrazono]propanedinitrile

Participants

Reaction Conditions

Reaction Steps

(+) 5-(4-aminophenyl)-6-methyl-3,6-dihydro-[1,3,4]-thiadiazin-2-one (1.34 g, 6 mmol) was dissolved in water (23 ml) and 6 N hydrochloric acid (4.5 ml). The solution was stirred and cooled. A cooled solution of sodiumnitrite (0.5 g) in water (5 ml) was added. Then a cooled solution of malononitrile (0.9 g) in t-butanol (54 ml) was added. In the end to the solution was added a cooled solution of sodium acetate (5.4 g) diluted in water (40 ml). The reaction mixture was stirred under cooling (0° C.) for 3 hours. After stirring the crystalline product was filtered and washed with water, yielding (+)-[[4-(3,6-dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)phenyl]hydrazono]propanedinitrile as a crystalline solid (1.7 g) with optical purity of 100%, chromatografic purity 99.3%, m.p. 125-128° C., [a]D25=+1002°.

Provenance & Evidence