Reaction #75478

Reaction equation

4-fluoroaniline

Nitric acid

cyanamide

→

title compound

Yield 47.0%

N-(4-Fluoro-phenyl)-guanidine nitrate

Yield 47.0%

Solvents

EtOH

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed under N2 for 21 h
2. 2
   OtherThe solvent was evaporated to dryness
3. 3
   WashThe solid residue was washed with EtOH
4. 4
   Otherdried under high vacuum overnight

Procedure

A solution of 4-fluoroaniline (25 mmol, 2.80 g) in EtOH (10 mL) was cooled on an ice bath. Nitric acid (69% aq. soln.; 1.8 mL) was added dropwise. Then cyanamide (50% aq. soln.; 4 mL) was added. The reaction mixture was refluxed under N2 for 21 h. The solvent was evaporated to dryness. The solid residue was washed with EtOH and dried under high vacuum overnight to afford the title compound as a purple powder (2.54 g, 47%). This material was used for subsequent reaction without further purification.

Source