3-Chlorobenzohydrazide → 2-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,3,4]oxadiazole

HRID 732043Notes

Reaction equation

HRID 732043 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].[Br:12][CH:13]([CH3:24])[C:14](OCC)(OCC)OCC>>[Br:12][CH:13]([C:24]1[O:6][C:5]([C:4]2[CH:9]=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)=[N:7][N:8]=1)[CH3:14]

Participants

3

Reactant 2

HCID 742893-ChlorobenzohydrazideHCID 27792852-Bromo-1,1,1-triethoxypropane

Product 1

HCID 670709782-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,3,4]oxadiazoleYield 32%

Procedure

3-Chloro-benzoic acid hydrazide (170 mg, 1 mmol) and 2-bromo-1,1,1-triethoxypropane (1 ml) were heated in a sealed vial at 120° C. for 10 min. The reaction mixture was place directly onto a flash column (silica gel) and purified using 0-50% dichloromethane in hexanes. The product was re-purified by flash column chromatography using a mixture of ethyl acetate:hexanes:dichloromethane (1:19:20) to afford 2-(1-bromo-ethyl)-5-(3-chloro-phenyl)-[1,3,4]oxadiazole (93 mg, 32%, colorless oil). 1H NMR (CDCl3) d (ppm): 8.09 (t, 1H), 7.99 (t, 1H), 7.55 (m, 3H), 5.30 (m, 1H), 2.21 (q, 3H).

Workup

  1. custompurified
  2. customThe product was re-purified by flash column chromatography
  3. additiona mixture of ethyl acetate:hexanes:dichloromethane (1:19:20)

Sources & evidence

ORD record
ord-1dc4b5b6b5284c6eaecdb60de2910ee8
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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