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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 884892Generated: October 31, 2026

Tetrahydrofuran → 6-Chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazole

https://huagongshe.com/reaction/884892

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
ReactantN-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamideHCID 66880038—
SolventTolueneHCID 1140—
Product6-Chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazoleHCID 6688176069.3%

Reaction Steps

To a mixture of 1.01 g of N-[4-chloro-2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 10 ml of tetrahydrofuran and 0.92 g of triphenylphosphine, 1.53 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature, and the reaction mixture was stirred for two hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant crystals washed with methanol to give 0.66 g of 6-chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 80”).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08242133B2
Source datasetuspto-grants-2012_08
ORD IDord-a02e72fd48a342eeafddb251076bfa91
Source noteuspto-grants-2012_08