Diphenylamine compounds and production method thereof

Patent metadata

Field	Value
Publication number	US-9550724-B2
Application number	US-201214361313-A
Country	US
Kind code	B2
Filing date	Dec 5, 2012
Priority date	Dec 14, 2011
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

An inexpensive and convenient production method of diphenylamine compounds is provided, that can solve problems in the conventional technology such as decrease in reactivity, restriction of substituents, high temperature, high pressure, by-products or the like. Further, diphenylamine compounds useful as intermediates of medicine and agricultural chemicals are provided. Diphenylamine compounds are produced, represented by general formula (3):

which is characterized by reacting aniline compounds represented by general formula (2):

under the presence of base and ethers solvent, with 2,6-dichloronitrobenzene compound represented by general formula (1):

and a diphenylamine compound represented by general formula (3).

First claim

The invention claimed is:

1. A method for producing diphenylamine compounds represented by general formula (3):

wherein, Z represents methoxy group at the para position of amine; m is 1; which is characterized by reacting aniline compounds represented by general formula (2):

wherein, Z and m are as defined above; under the presence of base and ethers solvent, with 2,6-dichloronitrobenzene compound represented by general formula (1):

wherein Y is halogen and n represents an integer of 0,
wherein 2.0 moles or more of aniline compound represented by general formula (2) is used relative to 1 mole of 2,6-dichloronitrobenzene compound represented by general formula (1) and 2.0 equivalents or more of base is used relative to 1 mole of 2,6-dichloronitrobenzene compound represented by general formula (1).

2. The method for producing diphenylamine compounds according to claim 1 , wherein the ethers solvent is tetrahydrofuran.

3. The method for producing diphenylamine compounds according to claim 1 , wherein the base is alkali metal hydride or alkali metal.

4. The method for producing diphenylamine compounds according to claim 1 , wherein the base is sodium hydride or sodium metal.

5. The method for producing diphenylamine compounds according to claim 1 , wherein the base is sodium hydride.

Assignees

• Ihara Chemical Ind Co
• Kumiai Chemical Industry Co

Inventors

• Ito Minoru
• Ikumi Akiko

Classifications

• C07C211/56

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title

• C07C209/10 Primary

  with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C213/02

  by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07C217/92

  the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring · CPC title