Reaction #75480

Reaction equation

2,4-difluoroaniline

nitric acid

cyanamide

→

title compound

Yield 40.0%

N-(2,4-Difluoro-phenyl)-guanidine nitrate

Yield 40.0%

Solvents

EtOH

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThe reaction mixture was refluxed under N2 for 22 h
3. 3
   OtherThe solvent was evaporated
4. 4
   WashThe solid residue was washed with EtOH
5. 5
   Otherwas dried under high vacuum

Procedure

To a mixture of 2,4-difluoroaniline (25 mmol, 3.2 g) in EtOH (10 mL) in an ice bath was added nitric acid (69% aq soln.; 1.8 mL) dropwise. After completion of the addition cyanamide (50% aq. soln.; 4 mL) was added. The reaction mixture was refluxed under N2 for 22 h. The solvent was evaporated. The solid residue was washed with EtOH and was dried under high vacuum to afford the title compound as a purple solid (2.32 g, 40%).

Source