Process for producing substituted methylamine compound and triazine derivative

Abstract

The present invention provides a process that enables a substituted methylamine compound which is useful as an intermediate for the production of agricultural chemicals and medicines, to be produced easily, with good yield, and at low cost, and also provides a production intermediate thereof. The process comprises a step of reacting a hexamethylenetetraammonium salt compound represented by a formula (I) with a base to obtain an N-methylidene-substituted methylamine oligomer represented by a formula (II) or a mixture of two or more of the oligomers, and a step of hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II) or the mixture of two or more of the oligomers in the presence of an acid. (wherein A represents an organic group, R represents a hydrogen atom, or an organic group, L represents a halogen atom and the like, and n represents an integer of 2 to 20)

1 - 13 . (canceled) 
     
     
         14 . An N-methylidene-pyridylmethylamine oligomer represented by a formula (II′) shown below: 
       
         
           
           
               
               
           
         
       
       wherein X represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group, and n represents an integer of 2 to 20. 
     
     
         15 . (canceled) 
     
     
         16 . A process for producing a substituted methylamine compound, said process comprising:
 hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II′) shown below in the presence of an acid,   
       
         
           
           
               
               
           
         
       
       wherein X represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group, and n represents an integer of 2 to 20, and
 producing a substituted methylamine compound represented by a formula (III) shown below: 
 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom and A represents a group represented by formula (IV) shown below: 
       
         
           
           
               
               
           
         
       
       wherein X is as defined above. 
     
     
         17 . The process for producing a substituted methylamine compound according to  claim 16 , wherein said A is a 2-chloropyridin-5-yl group. 
     
     
         18 . The process for producing a substituted methylamine compound according to  claim 16 , wherein hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II′) is conducted in at least one solvent selected from a group consisting of water, alcohol-based solvents, aliphatic hydrocarbon-based solvents, alicyclic hydrocarbon-based solvents, aromatic hydrocarbon-based solvents, ketone-based solvents, and ether-based solvents. 
     
     
         19 . The process for producing a substituted methylamine compound according to  claim 16 , wherein hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II′) is conducted at an temperature of within a range from room temperature to 90° C.