Methyl Isocyanate → HCID 53998651, compound

HRID 746117Notes

Reaction equation

HRID 746117 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[CH3:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[Cl:11]>C(Cl)(Cl)Cl>[CH3:1][NH:2][C:3]([N:9]1[C:10]([Cl:11])=[C:6]([CH3:5])[N:7]=[CH:8]1)=[O:4]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 178433268HCID 178433268, compound

Product 1

HCID 53998651HCID 53998651, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

104 g of methyl isocyanate were added dropwise to 233 g of 4-methyl-5-chloroimidazole in 1 liter of chloroform in a stirred flask provided with a thermometer and a reflux condenser. During the addition, the temperature increased to 40° C. Refluxing was carried out for 2 hours, the reaction solution was evaporated down under reduced pressure, the hot residue was dissolved in 400 ml of toluene, the solution was filtered with carbon and cooled, and the precipitated crystals were filtered off under suction, washed with toluene and dried to give 237 g (68.3%) of 1-N-methylcarbamyl-4-methyl-5-chloroimidazole of melting point 94.1°-94.4° C.

Workup

  1. customprovided with a thermometer and a reflux condenser
  2. additionDuring the addition
  3. temperatureRefluxing
  4. customthe reaction solution was evaporated down under reduced pressure
  5. dissolutionthe hot residue was dissolved in 400 ml of toluene
  6. filtrationthe solution was filtered with carbon
  7. temperaturecooled
  8. filtrationthe precipitated crystals were filtered off under suction
  9. washwashed with toluene
  10. customdried

Sources & evidence

ORD record
ord-f7e63a6ad34b4d479c55924f5de50534
Source dataset
uspto-grants-1986_07
Patent number
US04602927

Reaction notes

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