Acrylonitrile → 1-(2-Cyanoethyl)-4-nitroimidazole

HRID 1872909Notes

Reaction equation

HRID 1872909 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:16](#[N:19])[CH:17]=[CH2:18]>CN(C)C=O>[C:16]([CH2:17][CH2:18][N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]1)#[N:19]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 178526856HCID 178526856, compound

Product 1

HCID 110949891-(2-Cyanoethyl)-4-nitroimidazoleYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Nitroimidazole (6.87 g, 60 mmol), triethylamine (18.2 g, 180 mmol) and acrylonitrile (9.55 g, 180 mmol) were dissolved in N,N-dimethylformamide (100 ml), and the solution was stirred at 100° C. for 5 hours. The reaction mixture was concentrated under reduced pressure, and chloroform was added to the concentrate. Solids deposited were collected by filtration and dried to obtain 9.2 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and chloroform
  2. additionwas added to the concentrate
  3. filtrationSolids deposited were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-b5d2328da3db4029a73b11b5d8db2e88
Source dataset
uspto-grants-2000_08
Patent number
US06110967

Reaction notes

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