Reaction #6949

Reaction equation

NaOH

cyanamide

3-benzyloxyphenylamine

HCl

→

N-(3-Benzyloxy-phenyl)guanidine

Yield 98.4%

Solvents

1,4-dioxane

1,4-dioxane

Conditions

Workup

1. 1
   Temperaturethen cooled to ambient temperature
2. 2
   Filtrationthe resulting precipitate was collected by filtration
3. 3
   OtherThe solid product was dried under vacuum overnight
4. 4
   Otherto afford 23.8 g in 98.4% yield

Procedure

To a suspension of 3-benzyloxyphenylamine (20.0 g, 100.35 mmol) in 1,4-dioxane (150 mL) was added cyanamide (7.39 g, 175.95 mmol followed by 4M HCl in 1,4-dioxane (44 ml, 176.00 mmol). The resulting suspension was heated at 80° C. overnight then cooled to ambient temperature and 6N NaOH (35 ml, 210.00 mmol) was added. The volume of solution was reduced to 50 ml in vacuo and the resulting precipitate was collected by filtration. The solid product was dried under vacuum overnight to afford 23.8 g in 98.4% yield. 1H NMR (MeOH-d4) δ 6.4–7.5 (m, 9H), 5.1 (s, 2H).

Source