Dimethylformamide → (E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine

HRID 1847477Notes

Reaction equation

HRID 1847477 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C[C:16]([N:18]([CH3:20])[CH3:19])=O.CN(C=O)C>O>[F:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6](/[CH:8]=[CH:16]/[N:18]([CH3:20])[CH3:19])[CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31374DimethylacetamideHCID 5207051-Fluoro-5-methyl-2,4-dinitrobenzene

Product 1

HCID 15022335(E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamineYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-fluoro-5-methyl-2,4-dinitro-benzene (10 g, 50 mmol), DMA (12 g, 100 mmol) and DMF (50 mL) was heated at 100° C. for 4 h. The solution was cooled and poured into water. The precipitated red solid was collected, washed with water, and dried to give (E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine (8.0 g, 63%).

Workup

  1. temperatureThe solution was cooled
  2. customThe precipitated red solid was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-7bba44fce6764bd9a5746d77d4576040
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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