Reaktion #161138

ord-926eda6f61cd48d99f432d53abf418bf

Reaktionsgleichung

CCOC(=O)c1cc(C)c([N+](=O)[O-])cc1[N+](=O)[O-]
5-methyl-2,4-dinitro-benzoic acid ethyl ester
COC(OC)N(C)C
dimethoxymethyl-dimethylamine
→
CCOC(=O)c1cc(C=CN(C)C)c([N+](=O)[O-])cc1[N+](=O)[O-]
5-(2-dimethylamino-vinyl)-2,4-dinitro-benzoic acid ethyl ester
Ausbeute 32.3%

Edukte

CCOC(=O)c1cc(C)c([N+](=O)[O-])cc1[N+](=O)[O-]
5-methyl-2,4-dinitro-benzoic acid ethyl ester
COC(OC)N(C)C
dimethoxymethyl-dimethylamine
—
ice water

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe precipitate was collected via filtration
  2. 2
    Waschenwashed with water

Vorschrift

A mixture of 5-methyl-2,4-dinitro-benzoic acid ethyl ester (39 g, 0.15 mol) and dimethoxymethyl-dimethylamine (32 g, 0.27 mol) in DMF (200 mL) was heated at 100° C. for 5 h. The mixture was poured into ice water. The precipitate was collected via filtration and washed with water to afford 5-(2-dimethylamino-vinyl)-2,4-dinitro-benzoic acid ethyl ester (15 g, 28%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08829204B2uspto-grants-2014_09