Diethyl (ethoxymethylene)malonate → Diethyl 2-{[2-(trifluoromethyl)anilino]methylene}malonate
Reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>C1(C)C=CC=CC=1>[F:16][C:17]([F:25])([F:26])[C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([O:13][CH2:14][CH3:15])=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Diethyl ethoxymethylenemalonate (compound III, 50.4 mL, 249.3 mmol) and 2-(Trifluoromethyl)aniline (compound II, 31 mL, 249.3 mmol) was taken into toluene (250 mL) and refluxed overnight twice. Toluene was evaporated and the resulting liquid was taken into hexane and allowed to sit in a freezer for 1 hour. A white solid crashed out and was filtered and dried to yield 69.73 g (84.4%) of the title compound as white crystals. MS ESI (m/z) 332 ([M+H]+); MS ESI (m/z) 330 ([M−H]−); Anal Calcd. For C15H16F3NO4: C, 54.38; H, 4.87; N, 4.23. Found: C, 54.49; H, 4.68; N, 4.06.