1-Chloro-4-(chloromethyl)benzene → 1-(4-Chlorophenylmethyl)-2-aminobenzimidazole

HRID 1034212Notes

Reaction equation

HRID 1034212 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[N:6]([CH2:16][C:15]2[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 136242-Aminobenzimidazole

Product 1

HCID 7439001-(4-Chlorophenylmethyl)-2-aminobenzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-amino benzimidazole (6.66 g, 50 mmol), 4-chlorobenzylchloride (8.86 g, 55 mmol), and potassium carbonate (13.8 g, 100 mmol) in DMF (150 ml) was heated to 50° C. overnight. After dilution with water the product was filtered off. Recrystallization from water/ethanol 1:2 gave pure product. Yield 5.6 g (46%) mp 196°-197° C.

Workup

  1. filtrationAfter dilution with water the product was filtered off
  2. customRecrystallization from water/ethanol 1:2
  3. customgave pure product

Sources & evidence

ORD record
ord-b8e4be9f9b5e41f6b766a8fd9af51a3b
Source dataset
uspto-grants-1994_05
Patent number
US05314903

Reaction notes

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