[NH2:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[N:13]#[C:14][NH2:15].Cl.CO>O1CCOCC1.C(Cl)Cl>[OH:12][C:4]1[CH:3]=[C:2]([NH:1][C:14]([NH2:15])=[NH:13])[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=1
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.
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