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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 927034Generated: November 1, 2026

Water → HCID 76071552, compound

https://huagongshe.com/reaction/927034

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTriethylamineHCID 8471—
ReactantP,P-Diphenylphosphinic azideHCID 199401—
ReactantHCID 90203857HCID 90203857—
SolventDimethylformamideHCID 6228—
SolventHexaneHCID 8058—
SolventEthyl AcetateHCID 8857—
ProductHCID 76071552HCID 76071552—

Reaction Conditions

Temperature52.5 °C

Reaction Steps

A solution of 3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazole-4-carboxylic acid (1.0 g, 3.07 mmol) and triethylamine (0.5 mL, 3.4 mmol) in DMF (30 mL) was cooled to 0° C. Diphenylphosphorylazide (0.8 mL, 3.86 mmol) was added and the reaction mixture was warmed to 45-60° C. for 2 h. Water (15 mL) was then added and the reaction temperature increased to 90° C. for 28 h. The reaction mixture was cooled and 3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazol-4-ylamine was isolated by chromatography (5-40% ethyl acetate in hexane) as a white solid. m.p. 92-98° C. HRMS+1=297.123

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290465B2
Source datasetuspto-grants-2016_03
ORD IDord-eaff85ccad73471b8b7cd04727d5d0d9
Source noteuspto-grants-2016_03