Nitrite → N-Nitrosodiphenylamine

HRID 7265

Reaction equation

HRID 7265 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]([O-])=[O:15]>>[N:14]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:15]

Participants

3

Reactant 2

HCID 946NitriteHCID 11487Diphenylamine2×

Product 1

HCID 6838N-Nitrosodiphenylamine

Procedure

diphenylamine method, where diphenylamine as raw material is nitrosated using a nitrite in an organic solvent to produce N-nitrosodiphenylamine, which is rearranged to 4-nitrosodiphenylamine hydrochloride under the action of anhydrous hydrogen chloride, and then, 4-nitrosodiphenylamine hydrochloride is neutralized with a base to give 4-nitrosodiphenylamine which is finally reduced to 4-aminodiphenylamine by sodium sulfide.

Sources & evidence

ORD record
ord-e70b01ed6e6a4bcc904277bc74d3110e
Source dataset
uspto-grants-2006_08
Patent number
US07084302B2

Linked notes

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