Sulfuric Acid → Benzidine

HRID 1071897

Reaction equation

HRID 1071897 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.[Na+].[N+](C1C=CC=CC=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

8

Reactant 6

HCID 1118Sulfuric AcidHCID 66642-Nitrobenzenesulphonic acidHCID 7416NitrobenzeneHCID 14798Sodium HydroxideHCID 31222HydrazobenzeneHCID 31389Sodium 3-nitrobenzenesulfonate

Product 1

HCID 7111Benzidine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A 2-nitrobenzenesulfonic acid derivative (e.g. sodium 2-nitrobenzenesulfonate) or a 3-nitrobenzenesuflonic acid derivative (e.g. sodium 3-nitrobenzenesulfonate) and nitrobenzene are 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-c9827427759e481e95f5eb7980b46efa
Source dataset
uspto-grants-2005_06
Patent number
US06908719B1

Linked notes

Loading…