Dimethylamine → 4-(Dimethylamino)-3-(trifluoromethyl)benzonitrile

HRID 1961428Notes

Reaction equation

HRID 1961428 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH3:14][NH:15][CH3:16]>CS(C)=O.CCOC(C)=O>[CH3:14][N:15]([CH3:16])[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrile

Product 1

HCID 217328174-(Dimethylamino)-3-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Fluoro-3-(trifluoromethyl)benzonitrile (240 mg, 1.27 mmol) was dissolved in DMSO (1 ml) together with dimethylamine (1 ml, 40% aq). The mixture was stirred at r.t. for 18 hours followed by 4 hours at 50° C. The reaction was cooled, diluted with EtOAc (10 ml), washed with H2O (2*20 ml), dried over MgSO4 and evaporated to give 253 mg (93%) of the title substance as a greenish oil.

Workup

  1. waitfollowed by 4 hours at 50° C
  2. temperatureThe reaction was cooled
  3. washwashed with H2O (2*20 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give 253 mg (93%) of the title substance as a greenish oil

Sources & evidence

ORD record
ord-d3516dd8774c4f87ac0800a469488ddb
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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