Cyanogen Bromide → 1-(4-bromo-2-butynyl)-1,3-dihydro-3-methyl-2H-imidazol-2-one

HRID 846652Notes

Reaction equation

HRID 846652 reaction equation
N#[C:2][Br:3].C(N(CC)C[C:8]#[C:9][CH2:10][N:11]1[CH:15]=[CH:14][N:13]([CH3:16])[C:12]1=[O:17])C>O1CCOCC1>[Br:3][CH2:2][C:8]#[C:9][CH2:10][N:11]1[CH:15]=[CH:14][N:13]([CH3:16])[C:12]1=[O:17]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 150655321-[4-(Diethylamino)-2-butynyl]-1,3-dihydro-3-methyl-2H-imidazol-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Cyanogen bromide (6.0 g, 0.057 mol) was added to a stirred solution of 1-[4-(diethylamino)-2-butynyl]-1,3-dihydro-3-methyl-2H-imidazol-2-one in dioxane (130 mL). After evaporation of the dioxane, the residual oil was chromatographed on silica gel using chloroform:1% methanol as the eluant to give 10.8 g of 1-(4-bromo-2-butynyl)-1,3-dihydro-3-methyl-2H-imidazol-2-one as an oil.

Workup

  1. customAfter evaporation of the dioxane
  2. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-40c141d7961d465bb4ad8f3f47e88ae7
Source dataset
uspto-grants-1992_08
Patent number
US05137905

Reaction notes

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