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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 714653Generated: October 28, 2026

Potassium Carbonate → 4-Allyl-5-(4-chlorophenyl)-2-[(5-methyl-1H-imidazol-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

https://huagongshe.com/reaction/714653

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant4-hydroxymethyl-5-methyl-1H-imidazoleHCID 122433—
Reactant5-(4-chlorophenyl)-4-allyl-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 49765602—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product4-Allyl-5-(4-chlorophenyl)-2-[(5-methyl-1H-imidazol-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 67408340—

Reaction Steps

100 mg (0.89 mmol) of 4-hydroxymethyl-5-methyl-1H-imidazole, 252 mg (1.07 mmol) of the compound from Example 12A and 370 mg (2.68 mmol) of potassium carbonate were dissolved in 4.5 ml of DMF and 4.5 ml of water, and the mixture was stirred in a microwave oven at 200° C. for 75 min. After cooling to RT, for work-up, the mixture was diluted with 10 ml of water and extracted twice with in each case 15 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: first cyclohexane/ethyl acetate 1:1, then dichloromethane/methanol 10:1). This gave 153 mg (52% of theory) of the target compound in a purity of 73%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09187466B2
Source datasetuspto-grants-2015_11
ORD IDord-d8f567438b7443f99e1eed963f0aed00
Source noteuspto-grants-2015_11