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

HRID 225570Notes

Reaction equation

HRID 225570 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C)C=O>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]/[C:2]1[C:3]([C:11]([F:12])([F:13])[F:14])=[CH:4][CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 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)-Yield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 17 mmol 2-methyl-3-nitrobenzotrifluoride and 43 mmol N,N-dimethylformamide-dimethylacetal in 30 ml N,N-dimethylformamide was held at 120° C. overnight. The reaction mixture is concentrated in vacuo to give the crude title compound. Yield=83%. MS (m/e): 261.1 ([M+H]+, 90%).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-ffa2df15f24a4cd78dbf38159713a6b6
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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