Methane → 2-[[3-(Trifluoromethyl)phenyl]amino]acetonitrile

HRID 66772Notes

Reaction equation

HRID 66772 reaction equation
Cl[CH2:2][C:3]#[N:4].[NH2:5][C:6]1[CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:10][CH:11]=1.C([O-])([O-])=O.[K+].[K+].C>O.CS(C)=O>[F:15][C:12]([F:13])([F:14])[C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[NH:5][CH2:2][C:3]#[N:4]

Participants

7

Reactant 4

HCID 297MethaneHCID 73753-(Trifluoromethyl)anilineHCID 7856ChloroacetonitrileHCID 11430Potassium Carbonate

Product 1

HCID 128325572-[[3-(Trifluoromethyl)phenyl]amino]acetonitrileYield 73.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Chloroacetonitrile (16 g), m-aminobenzotrifluoride (32.2 g), K2CO3 (39.2 g) and DMSO (40 ml) were heated with stirring in a round-bottomed three-necked flask at 70°-80° C. for 4.0 hours. Pouring the reaction mixture into approximately 1 liter of ice and water resulted in the formation of an oil. The mixture was extracted with CH2Cl2 and the extracts obtained treated with diatomaceous earth and activated charcoal, and then filtered. The filtrate was taken to dryness, which gave 29.5 g of m-trifluoromethylanilinoacetonitrile as a dark oil.

Workup

  1. customresulted in the formation of an oil
  2. extractionThe mixture was extracted with CH2Cl2
  3. customthe extracts obtained
  4. filtrationfiltered

Sources & evidence

ORD record
ord-552c1bc43f6f4b34b2ae5680d3bae507
Source dataset
uspto-grants-1982_08
Patent number
US04343808

Reaction notes

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