Diethyl Ether → HCID 53889261, compound

HRID 443226Notes

Reaction equation

HRID 443226 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].[C:9]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1)#[N:10].C(OCC)C>C(#N)C>[C:9]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][N:7]=[CH:6]2)=[CH:13][CH:12]=1)#[N:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 869964-(Bromomethyl)benzonitrileHCID 178526856HCID 178526856, compound

Product 1

HCID 53889261HCID 53889261, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-nitroimidazole (2,25 g, 19.9 mmol) and 4-cyanobenzyl bromide (3.90 g, 19.9 mmol) in acetonitrile (10 ml) was stirred at 50° C. for 72 hrs. The reaction was allowed to cool to room temperature and diethyl ether (70 ml) was added. The precipitate was removed by filtration and the filtrate partitioned between EtOAc and NaHCO3 solution. The organic extract was dried (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed (SiO2, 5% MeOH in CH2Cl2) to afford a solid that was triturated with hot ethanol, and washed with diethyl ether, to afford the product as an off white solid.

Workup

  1. customThe precipitate was removed by filtration
  2. customthe filtrate partitioned between EtOAc and NaHCO3 solution
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. customThe residue was chromatographed (SiO2, 5% MeOH in CH2Cl2)
  7. customto afford a solid
  8. customthat was triturated with hot ethanol
  9. washwashed with diethyl ether
  10. customto afford the product as an off white solid

Sources & evidence

ORD record
ord-7e49efd378944289aa0dd746b62bd1da
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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