Water → HCID 19860304, compound

HRID 2072746Notes

Reaction equation

HRID 2072746 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+].O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[O:20])=[CH:15][C:14]=1[N+:29]([O-])=O>O1CCCC1>[NH2:29][C:14]1[CH:15]=[C:16]([C:19]([C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:22])=[O:20])[CH:17]=[CH:18][C:13]=1[NH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 19860301HCID 19860301, compound

Product 1

HCID 19860304HCID 19860304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation and polymerization of 3,4-diaminobenzil-A reduction solution made from sodium dithionite (0.6 grams), sodium hydroxide (0.3 grams) and water (10 ml) was stirred under nitrogen. 4-amino-3-nitrobenzil (270 mg) dissolved in tetrahydrofuran (4 ml) was added to the reduction solution. The color changed from pale yellow to dark brown indicating the progress of the reduction. Reaction was completed in 20 minutes and extraction by dichloromethane removed the organic layer. Drying with magnesium sulfate and solvent removal yielded the brown 3,4-diaminobenzil. Upon dissolving the 3,4-diaminobenzil in m-cresol and heating to 180° C. for 3 hours, complete polymerization took place. The polymerization is indicated by bleaching of the reddish brown monomer to a yellowish brown polymer, the polymer may be isolated by precipitation with methanol as yellowish brown powder from the cresol solution.

Workup

  1. additionwas added to the reduction solution
  2. customReaction
  3. extractionextraction by dichloromethane
  4. customremoved the organic layer
  5. dry with materialDrying with magnesium sulfate and solvent removal

Sources & evidence

ORD record
ord-6fe7acb904764811ba08b3a900f5c1c7
Source dataset
uspto-grants-1990_04
Patent number
US04914177

Reaction notes

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