Nitrogen → 1-(4-fluorophenyl)-2-(4-trifluoromethylphenyl)-N,N-dimethylethenylamine

HRID 968075

Reaction equation

HRID 968075 reaction equation
N#N.[H-].[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:15]([CH3:17])[CH3:16])[C:13]#N)=[CH:8][CH:7]=1.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:27]=[CH:26][C:23](CCl)=[CH:22][CH:21]=1>O.CN(C)C=O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:15]([CH3:17])[CH3:16])=[CH:13][C:23]2[CH:26]=[CH:27][C:20]([C:19]([F:29])([F:28])[F:18])=[CH:21][CH:22]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 947Nitrogen3×HCID 24758Sodium hydrideHCID 123096p-Trifluoromethylbenzyl chlorideHCID 11309856HCID 11309856, compound

Product 1

HCID 697465101-(4-fluorophenyl)-2-(4-trifluoromethylphenyl)-N,N-dimethylethenylamineYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Into a 200 ml four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a N2 gas supply tube, a N2 gas was introduced so that the interior of the flask became a N2 atmosphere. 40 ml of dimethylformamide and 2.4 g (61.6 mmol) of sodium hydride (62% oil suspension) were charged, and a solution comprising 10 g (56 mmol) of 2-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrile and 10.9 g (56 mmol) of 4-(trifluoromethyl)benzyl chloride, was dropwise added over a period of one hour at from 5 to 10° C. under cooling with ice water and then further reacted at from 20 to 30° C. for one hour. After completion of the reaction, 200 ml of water was added, and the mixture was extracted with 200 ml of ethyl acetate. The extract was washed with a 5% sodium hydrogen carbonate aqueous solution and water and then dried over anhydrous sodium sulfate. Ethyl acetate was distilled off, and the obtained oily substance was distilled under reduced pressure to obtain 15.3 g (yield: 88.3%) of the desired compound (boiling point: 130-135° C./0.6 KPa). The NMR spectrum data thereof were as follows.

Workup

  1. customInto a 200 ml four-necked flask equipped with a thermometer, a stirrer, a dropping funnel
  2. customfurther reacted at from 20 to 30° C. for one hour
  3. additionwas added
  4. extractionthe mixture was extracted with 200 ml of ethyl acetate
  5. washThe extract was washed with a 5% sodium hydrogen carbonate aqueous solution and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationEthyl acetate was distilled off
  8. distillationthe obtained oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-b9e99094524b4150b3b6d134605baecb
Source dataset
uspto-grants-2005_10
Patent number
US06956132B2

Linked notes

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