Reaction #2251

Reaction equation

cyanamide

3-trifluoromethyl-aniline

nitric acid

→

3-trifluoromethyl-phenylguanidine nitrate

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturethe reaction mixture is heated for 20 h under RF
2. 2
   TemperatureIt is then cooled to 0°
3. 3
   Filtrationfiltered
4. 4
   Washis washed with ethanol
5. 5
   Otherdried at 60° under HV

Procedure

6.3 g (150 mmol) of cyanamide (50% in water) are added to a suspension of 16.1 g (100 mmol) of 3-trifluoromethyl-aniline in 35 ml of ethanol. 7.0 ml of nitric acid (65%, 0.1 mol) are then added to the brown solution and the reaction mixture is heated for 20 h under RF. It is then cooled to 0° and filtered, and the material retained on the filter is washed with ethanol and dried at 60° under HV to give 3-trifluoromethyl-phenylguanidine nitrate; 1H-NMR (dimethyl sulfoxide): 7.6 (7H,m), 9.9 (1H,br,s).

Source