4-Chloroaniline → N-(4-Chlorophenyl)-N'-(trifluoromethyl)urea

HRID 1576684Notes

Reaction equation

HRID 1576684 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[F:9][C:10]([N:13]=[C:14]=[O:15])([F:12])[F:11]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14]([NH:13][C:10]([F:12])([F:11])[F:9])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 12494313Trifluoromethyl isocyanate

Product 1

HCID 19765994N-(4-Chlorophenyl)-N'-(trifluoromethyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-chloroaniline (64 grams; 0.5 mol) in toluene (100 ml) is placed into a suitable pressure vessel, and is cooled in an acetone-dry ice bath. Trifluoromethyl isocyanate (56 grams; 0.5 mol) is added thereto and the pressure vessel is sealed. The reaction mixture is allowed to warm up to room temperature and stand for a period of about 24 hours. After this time the pressure vessel is opened and the contents are stripped of toluene under reduced pressure. The residue is recrystallized to yield N-(4-chlorophenyl)-N'-trifluoromethyl urea.

Workup

  1. temperatureis cooled in an acetone-dry ice bath
  2. customthe pressure vessel is sealed
  3. customThe residue is recrystallized

Sources & evidence

ORD record
ord-8b0a73692b24420e930a9eed8eb030f1
Source dataset
uspto-grants-1976_09
Patent number
US03982019

Reaction notes

Loading…