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

HRID 53985

Reaction equation

HRID 53985 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-3d0d18ea8fa64a2b90025bea52f01bed
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Linked notes

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