Reaction #3029

Reaction equation

1-chloro-2,4-dinitrobenzene

sodium carbonate

dioctadecylamine

dimethylformamide

→

N,N-dioctadecyl-2,4-dinitrobenzenamine

Yield 87.2%

Solvents

water

Conditions

Workup

1. 1
   Temperaturewas heated to 80°-90° C. under a nitrogen atmosphere for 1 h
2. 2
   Extractionextracted with ether
3. 3
   WashThe extracts were washed with water
4. 4
   Dryingdried over magnesium sulfate
5. 5
   OtherThe solvent was removed
6. 6
   Otherthe solid recrystallized

Procedure

A mixture of 1-chloro-2,4-dinitrobenzene (Aldrich, 2.02 g, 10 mmol), sodium carbonate (1.27 g, 12 mmol), dioctadecylamine (Pfaltz & Bauer, 6.26 g, 12 mmol) and dry dimethylformamide (10 mL) was heated to 80°-90° C. under a nitrogen atmosphere for 1 h. The cooled mixture was diluted with water and extracted with ether. The extracts were washed with water and dried over magnesium sulfate. The solvent was removed and the solid recrystallized to give N,N-dioctadecyl-2,4-dinitrobenzenamine (6.0 g, 87%): mp 55.5°-57.5° C.

Source