Azobenzene → 4-Benzeneazodiphenylamine

HRID 53408Notes

Reaction equation

HRID 53408 reaction equation
[N:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[N:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>NC1C=CC=CC=1>[CH:12]1[CH:13]=[CH:14][C:9]([NH:1][C:12]2[CH:11]=[CH:10][C:9]([N:1]=[N:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 2272Azobenzene

Product 1

HCID 75754-BenzeneazodiphenylamineYield 90%

Reagents, catalysts & solvents 1

HCID 6115AnilineSolvent

Procedure

A solution of 25% aqueous tetramethylammonium hydroxide (8 mL) was concentrated under vacuum at 75° C. until solid material formed. Azobenzene (1.8 g) and aniline (10 mL) were added and the solution was stirred under the same conditions for 4 hours and then in the presence of air for 12 hours. Analysis of the reaction by HPLC revealed 90% yield of 4-(phenylazo)diphenylamine.

Workup

  1. concentrationA solution of 25% aqueous tetramethylammonium hydroxide (8 mL) was concentrated under vacuum at 75° C. until solid material
  2. customformed
  3. waitin the presence of air for 12 hours
  4. customAnalysis of the reaction by HPLC

Sources & evidence

ORD record
ord-f005c8cc4f594ec9a2333441f1c54644
Source dataset
uspto-grants-1997_04
Patent number
US05618979

Reaction notes

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