Dimethylformamide → HCID 73740491, compound

HRID 1371861Notes

Reaction equation

HRID 1371861 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].N1CCCC1.CO[CH:23](OC)[N:24]([CH3:26])[CH3:25].CN(C=O)C>C(OCC)(=O)C>[CH3:23][N:24]([CH:26]=[CH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])[CH3:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 12513084HCID 12513084, compound

Product 1

HCID 73740491HCID 73740491, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-methyl-2-nitro-4-trifluoromethoxybenzene (3.73 g, 16.86 mmol), pyrrolidine (1.32 g, 18.55 mmol), N,N-dimethylformamide dimethyl acetal (6.03 g, 50.58 mmol), and dry DMF (35 ml). Heat to about 105°. After 19 hours, remove the DMF under reduced pressure to give an oily residue. Combine the residue and ethyl acetate, wash with brine, dry (Na2SO4), then concentrate to give N,N-dimethyl-2-(2-nitro-4-trifluoromethoxyphenyl)vinylamine.

Workup

  1. temperatureHeat to about 105°
  2. customremove the DMF under reduced pressure
  3. customto give an oily residue
  4. washwash with brine
  5. dry with materialdry (Na2SO4)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-dfa049c0c1be48d0925b46e8169dd174
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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