Methyl Isocyanate → HCID 12797106, compound

HRID 484703Notes

Reaction equation

HRID 484703 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[CH2:17][CH3:18])=[CH:8][CH:7]=1>ClCCl>[CH2:17]([C:13]1[N:12]([C:9]2[CH:8]=[CH:7][C:6]([NH:5][C:3]([NH:2][CH3:1])=[O:4])=[CH:11][CH:10]=2)[CH:16]=[CH:15][N:14]=1)[CH3:18]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 12797132HCID 12797132, compound

Product 1

HCID 12797106HCID 12797106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.8 g of methyl isocyanate was added to a solution of 1.5 g of 1-(4-aminophenyl)-2-ethylimidazole in 20 ml of dichloromethane, and the mixture was stirred at room temperature for 3 hours and then refluxed with stirring for 3 hours. After completion of the reaction, the reaction mixture was naturally cooled and the solvent was removed by distillation under reduced pressure. Benzene was added to the residue, and the formed solid was recovered by filtration. The recovered solid was dissolved in a small quantity of methanol and recrystallized from an ethyl ether/benzene mixed solvent. The obtained compound was converted to a hydrochloride having a melting point of 228° to 232° C. according to customary procedures. Elementary analysis values as C13H16N4O.HCl were as follows.

Workup

  1. temperaturerefluxed
  2. stirringwith stirring for 3 hours
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was naturally cooled
  5. customthe solvent was removed by distillation under reduced pressure
  6. additionBenzene was added to the residue
  7. filtrationthe formed solid was recovered by filtration
  8. dissolutionThe recovered solid was dissolved in a small quantity of methanol
  9. customrecrystallized from an ethyl ether/benzene mixed solvent

Sources & evidence

ORD record
ord-bb8eede82b644b189ff16c5b4960dec9
Source dataset
uspto-grants-1985_08
Patent number
US04533669

Reaction notes

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