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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2094406Generated: October 25, 2026

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

https://huagongshe.com/reaction/2094406

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
ReactantN-[5-chloro-2-hydroxy-4-trifluoromethylphenyl]isonicotinamideHCID 66879747—
SolventTolueneHCID 1140—
Product5-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazoleHCID 6688021821.2%

Reaction Steps

To a mixture of 0.55 g of N-[5-chloro-2-hydroxy-4-(trifluoromethyl)phenyl]isonicotinamide, 6 ml of tetrahydrofuran and 0.50 g of triphenylphosphine, 0.83 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the resultant crystals were washed with methanol to give 0.11 g of 5-chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 78”).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08445522B2
Source datasetuspto-grants-2013_05
ORD IDord-87b439adc1da430d81d7ab67b699be7c
Source noteuspto-grants-2013_05