Diethyl Ether → 2-(1,3-Diphenyl-propenyl)-6-trifluoromethyl-phenylamine

HRID 643286Notes

Reaction equation

HRID 643286 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[CH2:20](OCC)[CH3:21].[C:25]1([Mg]CC)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-]>O>[C:14]1([C:12]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]=2[NH2:1])=[CH:20][CH2:21][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21555860HCID 21555860, compoundHCID 178461631HCID 178461631, compound

Product 1

HCID 685793302-(1,3-Diphenyl-propenyl)-6-trifluoromethyl-phenylamineYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2-Amino-3-trifluoromethyl-phenyl)-phenyl-methanone (0.26 g, 1.0 mmol) was taken into diethyl ether (20 mL) and phenyl ethyl magnesium chloride (1.5 mL, 1.5 mmol, 1.0 M solution in diethyl ether) was added dropwise and stirred at room temperature for 1 hour. The reaction was poured into water/saturated ammonium chloride solution and extracted with diethyl ether. The combined organics was dried over MgSO4 and concentrated. The material was purified via column chromatography using 0˜10% ethyl actetate in hexane as the eluent to yield 0.08 g (22%) of 2-(1,3-diphenyl-propenyl)-6-trifluoromethyl-phenylamine as an oil. MS ESI (m/z) 354.3 ([M+H]+);

Workup

  1. additionwas added dropwise
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organics was dried over MgSO4
  4. concentrationconcentrated
  5. customThe material was purified via column chromatography

Sources & evidence

ORD record
ord-e806b9ab942647fe9bdd942fa6e84fd1
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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