Triethylamine → N-Ethyl-N-(2,2-diethoxyethyl)-2,6-dinitro-4-trifluoromethylaniline

HRID 434468

Reaction equation

HRID 434468 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH2:18]([NH:20][CH2:21][CH:22]([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])[CH3:19].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:18]([N:20]([CH2:21][CH:22]([O:23][CH2:24][CH3:25])[O:26][CH2:27][CH3:28])[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 125032612,2-Diethoxy-N-ethylethan-1-amine

Product 1

HCID 20492547N-Ethyl-N-(2,2-diethoxyethyl)-2,6-dinitro-4-trifluoromethylaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4-Chloro-3,5-dinitrobenzotrifluoride (5.4 grams; 0.02 mole) dissolved in toluene (50 ml) and a solution of N-ethyl-N-(2,2-diethoxyethyl)amine (3.2 grams; 0.02 mole) and triethylamine (2.02 grams; 0.02 mole in toluene (50 ml) were charged into a glass reaction vessel equipped with stirrer, thermometer and reflux condenser. The mixture was heated at reflux overnight resulting in the formation of a precipitate. The reaction mixture was then filtered and the filtrate was washed with water, dried and stripped of solvent to yield the desired product N-ethyl-N-(2,2-diethoxyethyl)-2,6-dinitro-4-trifluoromethylaniline.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe 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 was washed with water
  8. customdried

Sources & evidence

ORD record
ord-e06ee16277c14ee9b483fa8182be6a7c
Source dataset
uspto-grants-1983_08
Patent number
US04397677

Linked notes

Loading…