Imidazole → 1,3-Dihydro-1-[4-(1H-imidazol-1-yl)-2-butynyl]-3-methyl-2H-imidazol-2-one

HRID 483635Notes

Reaction equation

HRID 483635 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][C:8]#[C:9][CH2:10][N:11]1[CH:15]=[CH:14][N:13]([CH3:16])[C:12]1=[O:17]>O1CCOCC1>[N:1]1([CH2:7][C:8]#[C:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]([CH3:16])[C:12]2=[O:17])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 150655461-(4-bromo-2-butynyl)-1,3-dihydro-3-methyl-2H-imidazol-2-one

Product 1

HCID 150655791,3-Dihydro-1-[4-(1H-imidazol-1-yl)-2-butynyl]-3-methyl-2H-imidazol-2-oneYield 79.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Imidazole (3.87 g, 0.057 mol) was added to a stirred solution of 1-(4-bromo-2-butynyl)-1,3-dihydro-3-methyl-2H-imidazol-2-one (3.26 g, 0.014 mol) in dioxane (50 mL). After 18 hr the dioxane was evaporated and the residue was chromatographed on silica gel to give 2.4 g of product.

Workup

  1. customAfter 18 hr the dioxane was evaporated
  2. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-3a4a367fc3824972ac27088d764cb2f4
Source dataset
uspto-grants-1993_07
Patent number
US05225567

Reaction notes

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