18-Crown-6 → 1-(2-Chlorobenzyl)-2-methylbenzimidazole-6-acetonitrile

HRID 276038Notes

Reaction equation

HRID 276038 reaction equation
[O-][C:2]#[N:3].[K+].C1OCCOCCOCCOCCOCCOC1.[Cl:23][C:24]1[CH:42]=[CH:41][CH:40]=[CH:39][C:25]=1[CH2:26][N:27]1[C:31]2[CH:32]=[C:33]([CH2:36]Cl)[CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[CH3:38]>CS(C)=O>[Cl:23][C:24]1[CH:42]=[CH:41][CH:40]=[CH:39][C:25]=1[CH2:26][N:27]1[C:31]2[CH:32]=[C:33]([CH2:36][C:2]#[N:3])[CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[CH3:38]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 11378442Potassium cyanateHCID 226203421h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-

Product 1

HCID 186809811-(2-Chlorobenzyl)-2-methylbenzimidazole-6-acetonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium cyanate (0.450 g) and 0.450 g of 18-crown-6 were added to a solution of 1.20 g of 1-(2-chlorobenzyl)-6-chloromethyl-2-methylbenzimidazole in 10 ml of dimethylsulfoxide, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was extracted with the addition of chloroform, water and a small amount of aqueous ammonia. The organic layer was concentrated, and the residue was purified through silica-gel column chromatography (eluent: a mixture of chloroform and methanol at a ratio of 20:1) to give 0.500 g of 1-(2-chlorobenzyl)-2-methylbenzimidazole-6-acetonitrile.

Workup

  1. extractionThe reaction mixture was extracted with the addition of chloroform, water
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified through silica-gel column chromatography (eluent
  4. additiona mixture of chloroform and methanol at a ratio of 20:1)

Sources & evidence

ORD record
ord-4ec5c6e3e3b14b689ae0ae8c0e55b205
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

Loading…