Diethyl (ethoxymethylene)malonate → Diethyl 2-{[2-(trifluoromethyl)anilino]methylene}malonate

HRID 2104472Notes

Reaction equation

HRID 2104472 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

HCID 6871Diethyl (ethoxymethylene)malonate2×HCID 69222-(Trifluoromethyl)aniline2×

Product 1

HCID 3107365Diethyl 2-{[2-(trifluoromethyl)anilino]methylene}malonateYield 84.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. temperaturerefluxed overnight twice
  2. customToluene was evaporated
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-5fd81fb35f3b42e7baa6128564e51574
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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