Diphosgene → 5-{2-[(Phenylmethyl)thio]phenyl}-1,3,4-oxadiazol-2(3H)-one
Reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[C:9]1([CH2:15][S:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([NH:21][NH2:22])=[O:20])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCOCC1>[C:9]1([CH2:15][S:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]2[O:20][C:2](=[O:3])[NH:22][N:21]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution containing 12.2 g of trichloromethyl chloroformate in 130 ml of p-dioxane was added portionwise 16 g of 2-[(phenylmethyl)thio]benzoic acid, hydrazide [prepared by the procedure of South African Patent Application 838,416 (1983)] to cause a slight exotherm to 37° C. After stirring at ambient temperature for 0.5 hr., the suspension was refluxed for 6 hours, then cooled to 25° C. and poured onto excess ice/water to yield a precipitate. The mixture was filtered, washed with water and the isolated solid was recrystallized from acetonitrile to yield 14 g of the subject compound; m.p. 169°-172° C.