Reaction #82263

Reaction equation

3,4-diaminobenzonitrile

ethyl chloroacetoimidate hydrochloride

→

2-chloromethyl-5-benzimidazolecarbonitrile

Yield 54.9%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturethe solution was refluxed
2. 2
   Temperatureunder heating for 3 hours
3. 3
   TemperatureAfter cooling
4. 4
   workup.DISTILLATIONdistilling off the solvent
5. 5
   workup.DISSOLUTIONthe resulting residue was dissolved in ethyl acetate
6. 6
   Washwashed with water
7. 7
   Otherdried
8. 8
   workup.DISTILLATIONAfter distilling off the solvent
9. 9
   Otherthe crystals thus precipitated
10. 10
    Filtrationwere collected by filtration

Procedure

3.42 g of 3,4-diaminobenzonitrile and 4.06 g of ethyl chloroacetoimidate hydrochloride were dissolved in 100 ml of ethanol, and the solution was refluxed under heating for 3 hours. After cooling and distilling off the solvent, the resulting residue was dissolved in ethyl acetate, washed with water, and then dried. After distilling off the solvent, the crystals thus precipitated were collected by filtration to obtain 2.7 g of 2-chloromethyl-5-benzimidazolecarbonitrile.

Source