Phenylurea → HCID 15557216, compound

Participants

Reaction Steps

To a solution of 1.33 g (5 millimole) of 5-amino-2-(p-tolyl)-4-phenylthiazole in 45 ml of benzene, 0.9 g (7.5 millimole) of the phenylisocyanate in 5 ml of anhydrous benzene is added at room temperature. The reaction mixture is refluxed for 3 hours and 0.45 g (3.75 millimole) of additional phenylisocyanate is added, refluxing is continued for an additional 3 hours, the reaction mixture is cooled and the insoluble part recovered by filtration under vaccum and washed with benzene. On crystallization from ethanol, 1.5 g of the corresponding phenylurea is obtained (M.p. 247°-263° C.; yield 78%). 25 Grams of the resulting 1-phenyl-3-[4-phenyl-2-(p-tolyl)-thiazol-5-yl]urea is heated on a metal bath to a temperature of 300°-305° C.; until aniline distills which, on condensing, dissolves phenylurea which has previously sublimed. After some minutes, the reaction mass is cooled and ethyl acetate-ethyl ether mixture is added thereto. On filtering under vacuum, a substance is recovered which, on crystallization from dimethylformamide, gives 19 g of the desired product (m.p. 314°-316° C.; yield 75%).

Provenance & Evidence