Water → 4,4'-[(2-Oxoimidazolin-1,3-diyl)bis(methylene)]-bis(benzonitrile)

HRID 1664

Reaction equation

HRID 1664 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].Br[CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.O>CN(C)C=O>[O:8]=[C:4]1[N:5]([CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH2:6][CH2:7][N:3]1[CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 84532-ImidazolidinoneHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 700916594,4'-[(2-Oxoimidazolin-1,3-diyl)bis(methylene)]-bis(benzonitrile)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a solid formed. The solid was filtered to give 4,4'-[(2-oxoimidazolin-1,3-diyl)bis(methylene)]-bis(benzonitrile). NMR (CDCl3) 7.65 (d,4), 7.4 (d,4), 4.45 (s,4), 3.2 (s,4) ppm.

Workup

  1. additionwas added
  2. customa solid formed
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-b8ac393b893c42cfb6d34015ef8c6939
Source dataset
uspto-grants-1998_03
Patent number
US05726198

Linked notes

Loading…