Reaction #65601

Reaction equation

4-(2,4-dimethylphenoxy)-2,5-dimethyl-3-chloroaniline

2,6-difluorobenzoyl isocyanate

→

1-[3-chloro-4-(2,4-dimethylphenoxyl)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl) urea

Solvents

toluene

toluene

hexane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated to a temperature of 90° C.
2. 2
   Temperaturemaintained at this temperature for 0.5 hours
3. 3
   TemperatureAfter cooling to room temperature
4. 4
   Temperaturecooled in an ice bath
5. 5
   OtherA precipitate formed which
6. 6
   Filtrationwas collected by filtration
7. 7
   Washwashed with a cold solution of 50% hexane in toluene
8. 8
   OtherAfter vacuum drying
9. 9
   Otherwas obtained

Procedure

Into a solution of 4-(2,4-dimethylphenoxy)-2,5-dimethyl-3-chloroaniline (1.75 grams, 6.3 mmol) prepared in Part B in 7 milliliters of toluene, which solution was warmed to a temperature of 50° C., was added 1.14 grams (6.2 mmol) of 2,6-difluorobenzoyl isocyanate in 1.5 milliliters of toluene. The reaction mixture was heated to a temperature of 90° C. and maintained at this temperature for 0.5 hours. After cooling to room temperature, the reaction mixture was diluted with 20 milliliters of hexane and then cooled in an ice bath. A precipitate formed which was collected by filtration and washed with a cold solution of 50% hexane in toluene. After vacuum drying, a white solid (1.26 grams) which was identified as 1-[3-chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl)urea was obtained having a melting point of 183° C.-185° C. Elemental analysis of the white solid indicated the following:

Source