Triethylamine → N-(2,2-Diethoxyethyl)-N-ethyl-4-methyl-2,6-dinitroaniline

HRID 434470Notes

Reaction equation

HRID 434470 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH2:15]([NH:17][CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])[CH3:16].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:15]([N:17]([CH2:18][CH:19]([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25])[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789184-Chloro-3,5-dinitrotolueneHCID 125032612,2-Diethoxy-N-ethylethan-1-amine

Product 1

HCID 20492554N-(2,2-Diethoxyethyl)-N-ethyl-4-methyl-2,6-dinitroaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-3,5-dinitrotoluene (4.32 grams; 0.02 mole), N-ethyl-N-(2,2-diethoxyethyl)amine (3.2 grams; 0.02 mole), triethylamine (2.02 grams; 0.02 mole) and toluene (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux overnight resulting in the formation of a precipitate. The reaction mixture was then filtered and the filtrate washed with water, dried and stripped of solvent to yield the desired product N-ethyl-N-(2,2-diethoxyethyl)-2,6-dinitro-p-toluidine.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux overnight
  5. customresulting in the formation of a precipitate
  6. filtrationThe reaction mixture was then filtered
  7. washthe filtrate washed with water
  8. customdried

Sources & evidence

ORD record
ord-b9624842cc48450d8ca1d1793312fb22
Source dataset
uspto-grants-1983_08
Patent number
US04397677

Reaction notes

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