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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1410145Generated: October 28, 2026

Diethyl Ether → HCID 67120049, compound

https://huagongshe.com/reaction/1410145

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantEthyl BromideHCID 6332—
ReactantLithium diisopropylamideHCID 2724682—
ReactantHCID 68156597HCID 68156597—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductHCID 67120049HCID 6712004923.3%

Reaction Steps

To 5-amino-3-ethyl-1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (0.50 g, 2.06 mmol) in THF (10 mL) at −78 C was added LDA (0.6 M in THF, 4.5 mL, 2.7 mmol) and stirred for 5 min, followed by EtBr (500 μL, 6.81 mmol) and the reaction was stirred over night at room temperature. Et2O and water were added, and the organic phase was separated. The water phase was acidified using 1 M HCl which was extracted with EtOAc. After drying using MgSO4, and evaporation of solvent the crude was purified using silica chromatography to give 3-ethyl-5-(ethylamino)-1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (130 mg, 23%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921402B2
Source datasetuspto-grants-2014_12
ORD IDord-3543ec459079404489a0941ffbcbbcea
Source noteuspto-grants-2014_12