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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2190767Generated: October 31, 2026

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

https://huagongshe.com/reaction/2190767

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 numberUS08324387B2
Source datasetuspto-grants-2012_12
ORD IDord-104eb10087a3450fbd534322932bfb74
Source noteuspto-grants-2012_12