Sodium Sulfate → 2,5-Dimethoxy benzoquinone diimine

HRID 653019

Reaction equation

HRID 653019 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([O:10][CH3:11])=[CH:5][C:4]=1[NH2:12].S([O-])([O-])(=O)=O.[Na+].[Na+]>[Ag]=O.C(OC(C)C)(C)C>[CH3:11][O:10][C:6]1[C:7](=[NH:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4](=[NH:12])[CH:5]=1

Participants

5

Reactant 2

HCID 24436Sodium Sulfate2×HCID 1555944-Amino-2,5-dimethoxyaniline

Product 1

HCID 539632862,5-Dimethoxy benzoquinone diimine

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 7914Diisopropyl EtherSolvent

Procedure

0.06 mole (10 g) 2,5-dimethoxy paraphenylene diamine is introduced into a liter of anhydrous isopropyl ether. 21 g silver oxide and 48 g anhydrous sodium sulfate are then added to the same. The resulting mixture is heated at reflux for 6 hours, while maintaining good agitation. After cooling the reaction mixture the sodium sulfate and the silver are filtered out and the filtrate is evaporated to dryness under vacuum. The dry residue which is the above diimine, after recrystallization from a benzene-petroleum ether mixture, yields pure 2,5-dimethoxy benzoquinone diimine having a melting point of 184°.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 6 hours
  3. temperaturewhile maintaining good agitation
  4. filtrationthe silver are filtered out
  5. customthe filtrate is evaporated to dryness under vacuum
  6. customafter recrystallization from a benzene-petroleum ether mixture

Sources & evidence

ORD record
ord-4457308020e748f0a313bb53c0dad321
Source dataset
uspto-grants-1987_06
Patent number
US04675130

Linked notes

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