Reaction #1265387

Reaction equation

MeOH

3-Amino-5-trifluoromethyl-phenol

cyanamide

HCl

→

N-(3-Hydroxy-5-trifluoromethyl-phenyl)-guanidine

Solvents

CH2Cl2

dioxane

dioxane

Conditions

Workup

1. 1
   OtherThe reaction was partitioned between ethyl acetate/saturated NH4Cl solution
2. 2
   Extractionextracted
3. 3
   Extractionafter multiple extractions

Procedure

A solution of 3-Amino-5-trifluoromethyl-phenol (0.21 g, 1.19 mmol), cyanamide (0.5 g, 1.19 mmol), 4N HCl in dioxane (2.975 ml, 1.199 mmol) in dioxane (10 ml) was heated in a sealed tube at 80° C. overnight resulting in complete conversion to product by TLC (10% MeOH:CH2Cl2). The reaction was partitioned between ethyl acetate/saturated NH4Cl solution and extracted. Some product remained in the aqueous phase after multiple extractions. The crude product (0.65 g, 0.297 mmol) was sufficiently pure by LC/MS to use directly for the next step.

Source