4-Chloro-3-methylaniline → N-(4-Chloro-3-methylphenyl)-N'-(trifluoromethyl)urea

HRID 1576685Notes

Reaction equation

HRID 1576685 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[F:10][C:11]([N:14]=[C:15]=[O:16])([F:13])[F:12]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][C:15]([NH:14][C:11]([F:13])([F:12])[F:10])=[O:16])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

4

Reactant 2

HCID 235364-Chloro-3-methylanilineHCID 12494313Trifluoromethyl isocyanate

Product 1

HCID 21511688N-(4-Chloro-3-methylphenyl)-N'-(trifluoromethyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-methyl-4-chloroaniline (70 grams; 0.5 mol) in toluene (150 ml) is placed into a pressure vessel, and is cooled in an acetone-dry ice bath. Trifluoromethyl isocyanate (56 grams; 0.5 mol) is added and the pressure vessel is sealed. The reaction mixture is warmed to about 25° C. and is allowed to stand for about 24 hours. After this time the reaction vessel is opened and its contents are stripped of toluene by evaporation under reduced pressure. The residue is then recrystallized to yield N-(3-methyl-4-chlorophenyl)-N'-trifluoromethyl urea.

Workup

  1. temperatureis cooled in an acetone-dry ice bath
  2. customthe pressure vessel is sealed
  3. customits contents are stripped of toluene by evaporation under reduced pressure
  4. customThe residue is then recrystallized

Sources & evidence

ORD record
ord-3271ce83b27049beab67e95b83b7175a
Source dataset
uspto-grants-1976_09
Patent number
US03982019

Reaction notes

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