Ethanol → Diisopropyl ether ethanol
Reaction equation
FC(F)(F)C1C=CC(CN([C:12]2[CH:17]=[CH:16]C(C#N)=CC=2)N)=CC=1.CO[CH:24]([O:29]C)[CH2:25]N=C=S.[CH2:31]([OH:33])[CH3:32]>>[CH:24]([O:29][CH:17]([CH3:16])[CH3:12])([CH3:31])[CH3:25].[CH2:31]([OH:33])[CH3:32]Participants
4
Procedure
To a suspension of N1-(4-trifluoromethylphenylmethyl)-N1-(4-cyanophenyl)hydrazine (7.5 g, 0.025 mol) in ethanol (100 ml) was added dropwise 2,2-dimethoxyethylisothiocyanate (4 g, 0.027 mol) and the reaction mixture was heated to reflux for 2 h. After cooling the solvent was evaporated under vacuum, the resulting residue was poured into 2N H2SO4 (20 ml) and the suspension was heated to reflux for 0.3 h. After extraction with ethyl acetate, the organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. Flash chromatography on silica gel (toluene/dioxane: 8/2) and trituration from diisopropyl ether/ethanol afforded a yellow solid (2.7 g, 28%), mp 200° C.