Diphosgene → 2-Methyl-5-phenylbenzylisocyanate

HRID 1883633Notes

Reaction equation

HRID 1883633 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[CH3:9][C:10]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][C:11]=1[CH2:12][NH2:13]>C1(C)C=CC=CC=1>[CH3:9][C:10]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][C:11]=1[CH2:12][N:13]=[C:4]=[O:3]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 235082132-Methyl-5-phenylbenzylamine

Product 1

HCID 120565262-Methyl-5-phenylbenzylisocyanateYield 99.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.5 g (12.6 mmol) of diphosgene, 0.40 g of activated carbon and 30 ml of toluene were mixed, and allowed to left overnight, and to this solution was slowly dropped at room temperature a solution prepared by dissolving 1.00 g (5.07 mmol) of 2-methyl-5-phenylbenzylamine (produced in the same manner as in Intermediate Production Example 6) in 5 ml of toluene. The reaction mixture turned to white suspension directly after the dropping. The white suspension was stirred at room temperature for 1 hour, further stirred for 5 hours under reflux with heating, then, concentrated under reduced pressure to obtain 1.13 g of 2-methyl-5-phenybenzyl isocyanate.

Workup

  1. additionto this solution was slowly dropped at room temperature a solution
  2. customprepared
  3. stirringfurther stirred for 5 hours
  4. temperatureunder reflux
  5. temperaturewith heating
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26cce3656c6f4abc91eef67c2c7d5502
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

Loading…