Malononitrile → HCID 86701180, compound

HRID 2206299Notes

Reaction equation

HRID 2206299 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=2[O:2]1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([F:21])[C:19]=1[F:20])[CH:15]=O.[C:22](#[N:26])[CH2:23][C:24]#[N:25].N1CCCCC1>C(O)C.O>[NH2:26][C:22]1[O:10][C:5]2[CH:4]=[C:3]3[O:2][CH2:1][O:9][C:8]3=[CH:7][C:6]=2[CH:15]([C:14]2[CH:13]=[C:12]([F:11])[C:19]([F:20])=[C:18]([F:21])[CH:17]=2)[C:23]=1[C:24]#[N:25]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 68289SesamolHCID 27769543,4,5-Trifluorobenzaldehyde

Product 1

HCID 86701180HCID 86701180, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3,4-Methylenedioxyphenol (166 mg, 1.2 mmol), 3,4,5-trifluorobenzaldehyde (160 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) were taken in 7 ml ethanol at room temperature, charged with piperidine (50 μL) and then stirred at 80° C. under LC-MS control till the reaction was complete. The reaction mixture was cooled down to room temperature, diluted with water to about 15 ml, stirred for 1 h, solids were collected by filtration, washed with 60% aq ethanol and dried (303 mg, 0.88 mmol, 88%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred for 1 h
  3. filtrationsolids were collected by filtration
  4. washwashed with 60% aq ethanol
  5. customdried (303 mg, 0.88 mmol, 88%)

Sources & evidence

ORD record
ord-1f7a8826f941432ca75afcaac923dfb6
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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