Reaction #165511

Reaction equation

4-chloro-3-(trifluoromethyl)phenyl isocyanate

p-phenylenediamine

→

N-(4-chloro-3-(trifluoromethyl)phenyl)-N′-(4-aminophenyl)urea

Yield 97.2%

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   Concentrationconcentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe resulting pink solids were dissolved in a mixture of EtOAc (110 mL) and MeOH (15 mL)
3. 3
   Washthe clear solution was washed with a 0.05 N HCl solution
4. 4
   ConcentrationThe organic layer was concentrated under reduced pressure

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)phenyl isocyanate (2.27 g, 10.3 mmol) in CH2Cl2 (308 mL) was added p-phenylenediamine (3.32 g, 30.7 mmol) in one part. The resulting mixture was stirred at room temp. for 1 h, treated with CH2Cl2 (100 mL), and concentrated under reduced pressure. The resulting pink solids were dissolved in a mixture of EtOAc (110 mL) and MeOH (15 mL), and the clear solution was washed with a 0.05 N HCl solution. The organic layer was concentrated under reduced pressure to afford impure N-(4-chloro-3-(trifluoromethyl)phenyl)-N′-(4-aminophenyl)urea (3.3 g): TLC (100% EtOAc) Rf 0.72.

Source