Methyl Isocyanate → HCID 53998651, compound

HRID 746121Notes

Reaction equation

HRID 746121 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[CH3:8][N:9]=[C:10]=[O:11]>C1(C)C=CC=CC=1>[CH3:8][NH:9][C:10]([N:5]1[C:6]([Cl:7])=[C:2]([CH3:1])[N:3]=[CH:4]1)=[O:11]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 178433268HCID 178433268, compound

Product 1

HCID 53998651HCID 53998651, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Using a procedure similar to that described in Example 1, 582.5 g of 4-methyl-5-chloroimidazole were dissolved in 1,500 ml of toluene at 70° C., and 313.5 g of methyl isocyanate were slowly run into the solution. During the addition, the temperature increased to about 90° C. Refluxing was then carried out for 30 minutes, after which the solution was cooled and then stirred for a further hour while being cooled with ice, and the precipitate which separated out was filtered off under suction, washed with ether and dried to give 826 g (95.2%) of 1-N-methylcarbamyl-4-methyl-5-chloroimidazole of melting point 95.6° C.

Workup

  1. additionDuring the addition
  2. temperatureRefluxing
  3. temperatureafter which the solution was cooled
  4. temperaturewhile being cooled with ice
  5. customthe precipitate which separated out
  6. filtrationwas filtered off under suction
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-1fec327901a04afaa79d2eb916e2fe42
Source dataset
uspto-grants-1986_07
Patent number
US04602927

Reaction notes

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