alpha-Chloro-o-xylene → 1-(o-Methylbenzyl)-imidazole-4,5-dinitrile

HRID 232094

Reaction equation

HRID 232094 reaction equation
[Na].[NH:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]#[N:10])[N:4]=[CH:3]1.[CH3:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Cl>C(O)C>[CH3:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][N:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]#[N:10])[N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 11093alpha-Chloro-o-xyleneHCID 707294,5-DicyanoimidazoleHCID 5360545Sodium

Product 1

HCID 200310241-(o-Methylbenzyl)-imidazole-4,5-dinitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.70 g of sodium are dissolved in 375 ml of ethanol and then 14.6 g of imidazole-4,5-dinitrile and 16.5 ml of o-methylbenzyl chloride are added and the whole is heated under reflux for 8 hours. The whole is concentrated to dryness by evaporation under reduced pressure and the residue is taken up in dichloromethane, washed in succession with water and with saturated sodium chloride solution, dried over sodium sulphate and concentrated to dryness by evaporation. The crude product is purified by chromatography on silica gel with toluene/ethyl acetate (5:1) and crystallised from ethyl acetate/hexane. 1-(o-methylbenzyl)-imidazole-4,5-dinitrile having a melting point of 80°-81° is obtained.

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe whole is concentrated to dryness by evaporation under reduced pressure
  4. washwashed in succession with water and with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness by evaporation
  7. customThe crude product is purified by chromatography on silica gel with toluene/ethyl acetate (5:1)
  8. customcrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-91f2bdda383f438383e49f6107c71af1
Source dataset
uspto-grants-1989_07
Patent number
US04851424

Linked notes

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