O-Xylene → N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)acetoacetamide

Participants

Reaction Steps

A 2-liter reaction flask with appropiate fittings was charged with 33.6 g (0.4 mole) of diketene, 965 ml of xylene and 59.7 g (0.38 mole) of 2-amino-5-tert-butyl-1,3,4-thiadiazole. The stirred mixture was heated to 70° at which time all solids had dissolved. After 1 hour, the solution was cooled and added to 2500 ml of chilled heptane. Product precipitation was judged complete after two hours. The solids were collected on a vacuum filter and air dried. There was obtained 54 g (58.9%) of white product, m.p. 166°-68°. N.M.R. (CDCl3 -dimethyl-d6 sulfoxide) ∂ 1.5 [C(CH3)3 ], 2.0 (CH3, enol), 2.3 (CH3, keto), 3.6 (CH2), 5.4 (CH, enol).

Provenance & Evidence