2-Nitrobenzamide → N-[(dimethylamino)ethylidene]-2-nitrobenzamide

HRID 1816299Notes

Reaction equation

HRID 1816299 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])([O-:3])=[O:2].CO[C:15](OC)([N:17]([CH3:19])[CH3:18])[CH3:16]>>[CH3:18][N:17]([CH2:15][CH:16]=[N:8][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:19]

Participants

3

Reactant 2

HCID 118762-NitrobenzamideHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Product 1

HCID 57019786N-[(dimethylamino)ethylidene]-2-nitrobenzamide

Conditions

Temperature
120 °C

Procedure

2-Nitrobenzamide (12.4 g, 75 mmol) was dissolved to dimethylacetamide-dimethylacetal (25 mL ) and heated to 120° C. for 2 hours. Upon cooling, the reaction was passed through a short silica column, eluting with ethyl acetate. The crystals that formed in the collected eluent were collected by filtration and rinsed with diethyl ether to provide N-[(dimethylamino)ethylidene]-2-nitrobenzamide (7.73 g).

Workup

  1. temperatureUpon cooling
  2. washeluting with ethyl acetate
  3. customThe crystals that formed in the collected eluent
  4. filtrationwere collected by filtration
  5. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-aa53b9ca7e0b408fa77a16147ab5a853
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

Loading…