Aniline → Acetanilide

HRID 229947Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](OC(=O)C)(=[O:10])[CH3:9]>>[C:8]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:10])[CH3:9]

Participants

Reactant 2

HCID 6115Aniline

HCID 7918Acetic Anhydride

Product 1

HCID 904Acetanilide

Procedure

For example, diarylamines may be produced using traditional Goldberg reactions. This method requires the derivatization of an aniline with acetic anhydride to produce an acetanilide compound. The acetanilide compound is then reacted with an arylbromide compound to produce an intermediate that must then be hydrolyzed in alcohol solution to produce the diarylamine compound. The formation of diphenylamines using the Goldberg reaction takes three reaction steps, and thus can be a lengthy process. Total cycle time for this process can be 3 to 5 days in the lab.

Sources & evidence

ORD record: ord-9f891c5a05af445595579ebf0b8862e3
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563932B2

Reaction notes

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