Dimethylacetamide → E-ethyl 5-(2-(dimethylamino)vinyl)-2,4-dinitrobenzoate

HRID 1908501Notes

Reaction equation

HRID 1908501 reaction equation
[CH3:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C[C:20]([N:22]([CH3:24])[CH3:23])=O>CN(C=O)C>[CH3:20][N:22]([CH3:24])/[CH:23]=[CH:1]/[C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 15184632Ethyl 5-methyl-2,4-dinitrobenzoate

Product 1

HCID 10590973E-ethyl 5-(2-(dimethylamino)vinyl)-2,4-dinitrobenzoateYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 5-methyl-2,4-dinitrobenzoate (39 g, 0.15 mol) and DMA (32 g, 0.27 mol) in DMF (200 mL) was heated at 100° C. for 5 h. The mixture was poured into ice water and the precipitated solid was filtered and washed with water to afford (E)-ethyl 5-(2-(dimethylamino)vinyl)-2,4-dinitrobenzoate (15 g, 28%).

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-6d3d17df01e5461c8135339af9334021
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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