Sodium Sulfate → 2-Methoxy-5-methyl benzoquinone diimine

HRID 1389733Notes

Reaction equation

HRID 1389733 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH2:11].S([O-])([O-])(=O)=O.[Na+].[Na+]>[Ag]=O>[CH3:10][O:9][C:5]1[C:6](=[NH:8])[CH:7]=[C:2]([CH3:1])[C:3](=[NH:11])[CH:4]=1

Participants

4

Reactant 2

HCID 24436Sodium SulfateHCID 957984-Amino-2-methoxy-5-methylaniline

Product 1

HCID 201952672-Methoxy-5-methyl benzoquinone diimineYield 69%

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

0.056 mole (8.56 g) 2-methyl-5-methoxy paraphenylenediamine is introduced into 850 cc isopropyl anhydrous ether to which there have been added 0.085 mole (19.7 g) silver oxide and 55 g anhydrous sodium sulfate. The mixture is agitated for two hours, maintaining the temperature thereof between 30° and 40°. After cooling, the sodium sulfate and silver are separated from the reaction mixture by filtration, and the resulting filtrate is evaporated to dryness under vacuum. The dry residue, after recrystallization from a mixture of benzene-hexane, furnishes 5.8 g 2-methoxy-5-methyl benzoquinone diimine, which has a melting point of 96°.

Workup

  1. temperaturemaintaining the temperature
  2. custombetween 30° and 40°
  3. temperatureAfter cooling
  4. customthe sodium sulfate and silver are separated from the reaction mixture by filtration
  5. customthe resulting filtrate is evaporated to dryness under vacuum
  6. customThe dry residue, after recrystallization
  7. additionfrom a mixture of benzene-hexane

Sources & evidence

ORD record
ord-4c5ba16293fb4f72b35b442ec4596595
Source dataset
uspto-grants-1981_01
Patent number
US04246181

Reaction notes

Loading…