Reaction #75474

Reaction equation

cyanamide

4-chloroaniline

nitric acid

→

title compound

Yield 44.0%

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

Yield 44.0%

Solvents

EtOH

Conditions

Workup

1. 1
   Temperaturerefluxed under N2 for a further 22 h
2. 2
   OtherThe solvent was evaporated
3. 3
   WashThe dark brown solid residue was washed with EtOH
4. 4
   Otherwas dried under high vacuum

Procedure

A solution of 4-chloroaniline (70 mmol, 8.88 g) in EtOH (5 mL) on an ice bath was treated with nitric acid (69% aq soln.; 5 mL). To this mixture cyanamide (50% aq. soln.; 5.4 mL) was added. The reaction mixture was stirred at r.t. for 10 min and then refluxed under N2 for a further 22 h. The solvent was evaporated. The dark brown solid residue was washed with EtOH and was dried under high vacuum to afford the title compound as a white powder (7.16 g, 44%). 1H-NMR (300 MHz, d6-DMSO) δ7.27-7.54 (m, 4H, Ph-H), 9.65 (br. s, 2H, NH).

Source