Aniline → N-Phenyl-N'-(trifluoromethyl)urea

HRID 1576682Notes

Reaction equation

HRID 1576682 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:8][C:9]([N:12]=[C:13]=[O:14])([F:11])[F:10]>C1(C)C=CC=CC=1>[C:2]1([NH:1][C:13]([NH:12][C:9]([F:11])([F:10])[F:8])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 12494313Trifluoromethyl isocyanate

Product 1

HCID 21511693N-Phenyl-N'-(trifluoromethyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of aniline (93.12 grams; 1.0 mol) in toluene (200 ml) is charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and gas inlet tube. Trifluoromethyl isocyanate (111 grams; 1.0 mol) is slowly bubbled into the reaction medium with vigorous stirring. The temperature of the reaction mixture is kept 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'-trifluoromethyl urea.

Workup

  1. customequipped with a mechanical stirrer
  2. customis kept below about 50° C
  3. additionAfter the addition
  4. customThe residue is then recrystallized

Sources & evidence

ORD record
ord-00be095e60074bec9eb2b08e9e7517e9
Source dataset
uspto-grants-1976_09
Patent number
US03982019

Reaction notes

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