HCID 23461201, compound → Azobenzene

HRID 580021Notes

Reaction equation

HRID 580021 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:9]=[N:10][C:11]2[CH:16]=[C:15](Cl)[CH:14]=[C:13](Cl)[CH:12]=2)[CH:5]=[C:6](Cl)[CH:7]=1>[O-2].[O-2].[Mn+4]>[N:9]([C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1)=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 23461201HCID 23461201, compound

Product 1

HCID 2272AzobenzeneYield 10%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

The oxidation of substituted anilines to azobenzenes is a well-known procedure; oxidizing agents of various sorts are employed. Wheeler and Gonzalez (Reference 6) used manganese dioxide as their oxidizing agent; with this reagent they oxidized 3,5-dichloroaniline (II) to the corresponding 3,5,3'5'-tetrachloroazobenzene (VI) in yields above 90%. Wheeler and Gonzalez report their technique gives only a 10% yield of azobenzene when applied to 3,5-dichloro-4-nitroaniline (VII). ##STR3##

Sources & evidence

ORD record
ord-39355642e06a4895be445178adaf1ac6
Source dataset
uspto-grants-1988_06
Patent number
US04751289

Reaction notes

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