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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 530793Generated: October 30, 2026

Ethyl Acetate → 4-(azidomethyl)-5-chloro-1,3-dimethyl-1H-pyrazole

https://huagongshe.com/reaction/530793

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantP,P-Diphenylphosphinic azideHCID 199401—
Reactant(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methanolHCID 13673186—
SolventTolueneHCID 1140—
Product4-(azidomethyl)-5-chloro-1,3-dimethyl-1H-pyrazoleHCID 61373454—

Reaction Steps

To a solution of compound 2 (538 mg, 3.36 mmol) in toluene (10 mL) was added DPPA (1.1 mL, 5.04 mmol) and DBU (0.6 mL, 6.72 mmol) at 0° C. After stirring for 1 hr, the reaction mixture was warmed to room temperature and stirred for 24 hr. EA (20 mL) was added and the mixture was washed with water, brine, concentrated to give a yellow solid which was used without further purification. LCMS (ESI) m/z=186 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09353104B2
Source datasetuspto-grants-2016_05
ORD IDord-bbdd22a442f946d58134a1e30e1dea0f
Source noteuspto-grants-2016_05