Sulfuric Acid → Benzidine

HRID 1071893Notes

Reaction equation

HRID 1071893 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1S(O)(=O)=O)([O-])=O.[N+:14]([C:17]1[CH:18]=[C:19](S(O)(=O)=O)[CH:20]=[CH:21][CH:22]=1)([O-])=O.[OH-].[Na+].N(C1C=CC=CC=1)NC1C=CC=CC=1.S(=O)(=O)(O)O>[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:20]2[CH:19]=[CH:18][C:17]([NH2:14])=[CH:22][CH:21]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 66642-Nitrobenzenesulphonic acidHCID 73873-Nitrobenzenesulfonic acidHCID 14798Sodium HydroxideHCID 31222Hydrazobenzene

Product 1

HCID 7111Benzidine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A 2-nitrobenzenesulfonic acid derivative (e.g. sodium 2-nitrobenzenesulfonate) or a 3-nitrobenzenesulfonic acid derivative (e.g. sodium 3-nitrobenzenesulfonate) is treated with zinc dust in the presence of an alkali (e.g. sodium hydroxide) and the resulting hydrazobenzene derivative is treated with sulfuric acid to give the corresponding 4,4′-diaminobiphenyl derivative. This is diazotized using sodium nitrite under acidic conditions in the presence of hydrochloric acid, followed by reaction with sodium azide, to give the desired product.

Sources & evidence

ORD record
ord-072c0e4795c747fb819cc6e9d2dae4d3
Source dataset
uspto-grants-2005_06
Patent number
US06908719B1

Reaction notes

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