4-Octoxybenzoyl hydrazine → 3,5-dibromo-N'-[4-(octyloxy)benzoyl]benzohydrazide

HRID 458492

Reaction equation

HRID 458492 reaction equation
BrC1C=CC(Br)=CC=1C1[O:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:16][CH:15]=2)=[N:12][N:13]=1.[Br:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([Br:39])[CH:38]=1)[C:33](Cl)=[O:34].C(OC1C=CC(C(NN)=O)=CC=1)CCCCCCC>>[Br:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([Br:39])[CH:38]=1)[C:33]([NH:13][NH:12][C:11](=[O:10])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:16][CH:15]=1)=[O:34]

Participants

4

Reactant 3

HCID 42815334-Octoxybenzoyl hydrazineHCID 134505263,5-Dibromobenzoyl chlorideHCID 219820732-(2,5-Dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole

Product 1

HCID 219820813,5-dibromo-N'-[4-(octyloxy)benzoyl]benzohydrazideYield 36%

Procedure

By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole in Example 1, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octyloxybenzoic acid hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave the required 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (6.12 g, 52% yield).

Sources & evidence

ORD record
ord-def7b1a82ede453eb42287d0f43d1b25
Source dataset
uspto-grants-2007_03
Patent number
US07192657B2

Linked notes

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