Water → Ethenamine, N,N-dimethyl-2-[2-nitro-6-(trifluoromethyl)phenyl]-, (1E)-

HRID 2278638Notes

Reaction equation

HRID 2278638 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=1[C:19]([F:22])([F:21])[F:20].O>CN(C)C=O>[CH3:5][N:4]([CH3:6])/[CH:3]=[CH:9]/[C:10]1[C:11]([C:19]([F:22])([F:21])[F:20])=[CH:12][CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 81171alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene

Product 1

HCID 57753441Ethenamine, N,N-dimethyl-2-[2-nitro-6-(trifluoromethyl)phenyl]-, (1E)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

3.5 ml of DMF-DMA (N,N-dimethylformamide-dimethyl acetal) are added to a solution of 1 g of 2-methyl-3-nitrobenzotrifluoride in 6 ml of N,N-dimethylformamide. The reaction medium is heated at 110° C. until the starting material has disappeared, then poured into water and extracted with ethyl acetate. The organic phases are washed successively with a 10% sodium bicarbonate solution, a 10% ammonium chloride solution and a saturated sodium chloride solution, dried over magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure so as to give 1.2 g of dimethyl[(E)-2-(2-nitro-6-trifluoromethylphenyl)vinyl]amine in the form of an oil which is used in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed successively with a 10% sodium bicarbonate solution
  3. dry with materiala 10% ammonium chloride solution and a saturated sodium chloride solution, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure so as

Sources & evidence

ORD record
ord-37fc85a07e7542dbbd9139fcafecbd62
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

Loading…