1-Chloro-2,4-Dinitrobenzene → N,N-dioctadecyl-2,4-dinitrobenzenamine

HRID 341896

Reaction equation

HRID 341896 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+].[CH2:20]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].CN(C)C=O>O>[CH2:39]([N:38]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 66989Dioctadecylamine

Product 1

HCID 21585066N,N-dioctadecyl-2,4-dinitrobenzenamineYield 87.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperaturewas heated to 80°-90° C. under a nitrogen atmosphere for 1 h
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed
  6. customthe solid recrystallized

Sources & evidence

ORD record
ord-2079cff997264068a9d3a4b8bdb2f8d7
Source dataset
uspto-grants-1999_01
Patent number
US05856431

Linked notes

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