1-Chloro-2,4-Dinitrobenzene → HCID 18345546, compound

HRID 590638

Reaction equation

HRID 590638 reaction equation
[CH2:1]([C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].CN1C=CN=C1.[N+:29]([C:32]1[CH:37]=[C:36]([N+:38]([O-])=O)[CH:35]=[CH:34][C:33]=1Cl)([O-])=O>C(C(C)=O)C>[CH2:1]([C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][C:35]1[CH:34]=[CH:33][C:32]([NH2:29])=[CH:37][C:36]=1[NH2:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 13901-MethylimidazoleHCID 68146Hydrogenated cardanol

Product 1

HCID 18345546HCID 18345546, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-(-3-Pentadecylphenoxy)benzene-1,3-diamine is prepared as described in chapter 2 of Jinu Suju Mathew, “Novel Thermally Stable Polymers from a Renewable Resource (Cashew Nut Shell Liquid): Thesis, Characterization, and Applications,” Ph.D. Thesis, U. of Pune, July 2001, the disclosure of which is totally incorporated herein by reference. More specifically, to a 100 mL three necked round bottom flask equipped with a reflux condenser, thermowell, and magnetic stirrer is added 5 g (0.016 mol) of 3-pentadecylphenol, 1.35 g (1.3 mL, 0.016 mol) of N-methyl imidazole, and 50 mL methyl ethyl ketone, and the solution is stirred for 1.5 hours. Thereafter 3.33 g (0.016 mol) of 2,4-dinitrochlorobenzene is added to this mixture and the reaction mixture is refluxed for 3 hours. The solvent is then distilled off and the residue dissolved in ether. The ether solution is then washed with water, 5% NaOH solution, and again with water. The ether solution is then dried with sodium sulfate and the ether distilled off to obtain the crude product. The crude product is then recrystallized from petroleum ether at 40 to 60° C. to obtain pure 1-(3-pentadecylphenoxy)-2,4-dinitrobenzene, of the formula

Workup

  1. temperaturethe reaction mixture is refluxed for 3 hours
  2. distillationThe solvent is then distilled off
  3. dissolutionthe residue dissolved in ether
  4. washThe ether solution is then washed with water, 5% NaOH solution
  5. dry with materialThe ether solution is then dried with sodium sulfate
  6. distillationthe ether distilled off
  7. customto obtain the crude product

Sources & evidence

ORD record
ord-7b06979d1d574d44ac3e2581ae073b9d
Source dataset
uspto-grants-2016_01
Patent number
US09234109B2

Linked notes

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