3,5-Dichlorobenzoyl chloride → 3,5-dichloro-N'-[4-(octyloxy)benzoyl]benzohydrazide

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Reaction Steps

By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (1) in Example 3, the reaction of 3,5-dichlorobenzoyl chloride (20.0 g, 0.010 mole) with 4-octoxybenzoyl hydrazide (25.24 g, 0.010 mole) gave the intermediate 3,5-dichloro-N′-[4-(octyloxy)benzoyl]benzohydrazide (25 g, 60% yield). Cyclocondensation of the intermediate 3,5-dichloro-N′-[4-(octyloxy)benzoyl]-benzohydrazide (16.0 g) with POCl3 (83 mL) gave the required 2-(3,5-dichlorophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (4) (11.16 g, 73% yield).

Provenance & Evidence