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

HRID 399093

Reaction equation

HRID 399093 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-c452d77aca5c4d06a3732c571f03370d
Source dataset
uspto-grants-1998_10
Patent number
US05817743

Linked notes

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