4-Fluorobenzohydrazide → HCID 17951329, compound

HRID 2406483Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12](OC(OCC)OCC)C>>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][CH:12]=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 99724-Fluorobenzohydrazide

HCID 31214Ethyl orthoformate

Product 1

HCID 17951329HCID 17951329, compoundYield 57%

Procedure

A stirred solution of 4-fluorobenzohydrazide (4.2 g, 27.2 mmol) in triethylorthoformate (27 mL) was heated at 140° C. for 5 h. The reaction was evaporated under reduced pressure. The crude was purified by silica gel column chromatography (100-200 mesh; using 12% ethyl acetate in hexane) to afford 2-(4-fluorophenyl)-1,3,4-oxadiazole [Polshettiwar, Tetrahedron Letters, 49:879-883 (2008)] as off-white solid (2.5 g, 57% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.46 (s, 1H), 8.08 (dd, 2H), 7.19 (dd, 2H); LC-MS m/z calculated for [M+H]+ 165.04, found 165.00.

Workup

customThe reaction was evaporated under reduced pressure
customThe crude was purified by silica gel column chromatography (100-200 mesh; using 12% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-18ccf86b69664b68be7b6c49f39918ac
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809372B2

Reaction notes

Loading…