Water → (E)-2-(5-chloro-2,4-dinitrophenyl)-N,N-dimethylethenamine

HRID 1847810Notes

Reaction equation

HRID 1847810 reaction equation
[Cl: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.O>CN(C=O)C>[Cl: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 962WaterHCID 31374DimethylacetamideHCID 2538025-Chloro-2,4-dinitrotoluene

Product 1

HCID 59129321(E)-2-(5-chloro-2,4-dinitrophenyl)-N,N-dimethylethenamineYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-chloro-5-methyl-2,4-dinitro-benzene (11.6 g, 50.0 mmol), DMA (11.9 g, 100 mmol) in 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 by filtration, washed with water, and dried to give (E)-2-(5-chloro-2,4-dinitrophenyl)-N,N-dimethylethenamine (9.84 g, 72%).

Workup

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

Sources & evidence

ORD record
ord-3bb4bd6e2a904bab8c23e31967ad4026
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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