3,4-Diaminobenzonitrile → 2-(Chloromethyl)-1H-benzo[d]imidazole-6-carbonitrile

HRID 1901351Notes

Reaction equation

HRID 1901351 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].Cl.[Cl:12][CH2:13][C:14](=N)OCC>C(O)C>[Cl:12][CH2:13][C:14]1[NH:1][C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=2[N:10]=1

Participants

4

Reactant 2

HCID 7372853,4-DiaminobenzonitrileHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochloride

Product 1

HCID 218444532-(Chloromethyl)-1H-benzo[d]imidazole-6-carbonitrileYield 54.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 3 hours
  3. temperatureAfter cooling
  4. distillationdistilling off the solvent
  5. dissolutionthe resulting residue was dissolved in ethyl acetate
  6. washwashed with water
  7. customdried
  8. distillationAfter distilling off the solvent
  9. customthe crystals thus precipitated
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-9f0d54ad97a44a509a1348fd91dfa50f
Source dataset
uspto-grants-1996_11
Patent number
US05576343

Reaction notes

Loading…