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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2359091Generated: November 2, 2026

Methyl iodide → HCID 67260331, compound

https://huagongshe.com/reaction/2359091

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
ReactantAmmonium ChlorideHCID 25517—
ReactantHCID 67260636HCID 67260636—
SolventDimethylformamideHCID 6228—
ProductHCID 67260331HCID 6726033154.4%

Reaction Conditions

Temperature0 °C

Reaction Steps

4-Bromo-3-(5-chloro-2-thienyl)-5-methyl-1H-pyrazole (35.3 mmol) was dissolved in 30 mL dry N,N-dimethylformamide and cooled to 0° C. under nitrogen atmosphere. Sodium hydride (37.1 mmol, 60% dispersion in mineral oil) was added in portions at 0° C. After stirring for 30 min, iodomethane (42.4 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The solution was poured into saturated aqueous ammonium chloride solution and extracted with diethyl ether, dried over MgSO4, filtered and evaporated. The crude product was purified by chromatography on silica gel (100% dichloromethane) to afford 5.6 g 4-bromo-3-(5-chloro-2-thienyl)-1,5-dimethyl-1H-pyrazole (54% yield)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08685974B2
Source datasetuspto-grants-2014_04
ORD IDord-7f6d8929cb1b4c249ea4923371024b3d
Source noteuspto-grants-2014_04