Dimethyl Sulfoxide → (1-benzyl-1H-imidazol-2-yl)acetonitrile

HRID 1253031Notes

Reaction equation

HRID 1253031 reaction equation
[C-:1]#[N:2].[Na+].CS(C)=O.Cl.[CH2:9]([N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21]Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[CH2:9]([N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21][C:1]#[N:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 27792431-benzyl-2-(chloromethyl)-1H-imidazole hydrochloride

Product 1

HCID 817477(1-benzyl-1H-imidazol-2-yl)acetonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Dry, powdered sodium cyanide (14 gm, 280 mmole) was added to 80 ml of dry dimethylsulfoxide with stirring at 23° C. Then 1-benzyl-2-chloromethylimidazole hydrochloride (14 gm, 63 mmole) was added portionwise over 10 minutes while maintaining the temperature below 40° C. After the addition was complete, the mixture was stirred at 40° C. for an additional hour. It was diluted with 250 ml methylene chloride and the resulting solution was washed with 4×200 ml of water, dried over MgSO4 and the solvent removed in vacuo. The residue was collected by filtration, dissolved in warm methanol and precipitated with ether to obtain needle-like crystals (8.7 g) of N-benzyl-2-cyanomethylimidazole. m.p. 102.5°-104° C.

Workup

  1. customDry
  2. temperaturewhile maintaining the temperature below 40° C
  3. additionAfter the addition
  4. stirringthe mixture was stirred at 40° C. for an additional hour
  5. washthe resulting solution was washed with 4×200 ml of water
  6. dry with materialdried over MgSO4
  7. customthe solvent removed in vacuo
  8. filtrationThe residue was collected by filtration
  9. dissolutiondissolved in warm methanol
  10. customprecipitated with ether

Sources & evidence

ORD record
ord-0b1e89ca57df41b2b83c32e76e0a5fab
Source dataset
uspto-grants-1988_05
Patent number
US04746669

Reaction notes

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