Toluene → N-Phenyl-N-propan-2-yl-N'-(trifluoromethyl)urea

HRID 1576683Notes

Reaction equation

HRID 1576683 reaction equation
C[NH:2][C:3]1[CH:8]=CC=C[CH:4]=1.[F:9][C:10]([N:13]=[C:14]=[O:15])([F:12])[F:11].[C:16]1(C)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:16]1([N:2]([CH:3]([CH3:8])[CH3:4])[C:14]([NH:13][C:10]([F:12])([F:11])[F:9])=[O:15])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 7515N-MethylanilineHCID 12494313Trifluoromethyl isocyanate

Product 1

HCID 21511695N-Phenyl-N-propan-2-yl-N'-(trifluoromethyl)urea

Procedure

A solution of N-methylaniline (10.7 grams; 0.1 mol) in toluene (100 ml) is charged into a glass reaction flask equipped with stirrer, thermometer and gas inlet tube. Trifluoromethyl isocyanate (11.1 grams; 0.1 mol) is slowly bubbled into the reaction medium with vigorous stirring and sufficient cooling to keep the temperature of the reaction mixture below about 50° C. After the addition is completed the reaction mixture is stirred for an additional period of about 1 hour. After this time the toluene is stripped from the reaction mixture under reduced pressure. The residue is then recrystallized to yield N-phenyl-N-isopropyl-N'-trifluoromethyl urea.

Workup

  1. customequipped with stirrer
  2. temperaturesufficient cooling
  3. customthe temperature of the reaction mixture below about 50° C
  4. additionAfter the addition
  5. stirringis stirred for an additional period of about 1 hour
  6. customThe residue is then recrystallized

Sources & evidence

ORD record
ord-2683f122f73047c48aa1d84389ed5d35
Source dataset
uspto-grants-1976_09
Patent number
US03982019

Reaction notes

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