Process for producing alkoxyiminoacetamide derivatives

Details Process for producing alkoxyiminoacetamide derivatives Process for producing alkoxyiminoacetamide derivatives

1997-02-26

2000-03-14

Kumar, Shailendra

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564163, C07C23305, C07C23108

Patent

active

060374950

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a process for producing an alkoxy(or hydroxy)iminoacetamide derivative and to intermediates for the production. Specifically, the present invention relates to a process for producing a 2-(2-hydroxymethylphenyl)-2-alkoxy(or hydroxy)iminoacetamide derivative useful as an intermediate for the production of alkoxyiminoacetamide compounds having potent fungicidal activity, and to intermediates for the production.


BACKGROUND OF THE INVENTION

2-(2-Hydroxymethylphenyl)-2-alkoxy(or hydroxy)iminoacetamide derivative is useful as an intermediate for the production of alkoxyiminoacetamide compounds useful as agricultural fungicides (JP-A 3-246268, JP-A 4-182461), and various processes for producing it have been known (JP-A 3-246268, JP-A 5-097768). However, there is still a room for improvement of these methods, and it has been desired to develop superior industrial processes for the production.
The object of the present invention is to provide a safe and industrially advantageous process for producing an intermediate for the production of alkoxyiminoacetamide compounds useful as agricultural fungicides and also to provide intermediates for the production.


DISCLOSURE OF THE INVENTION

The present inventors have intensively studied to achieve the above object. As a result, it has been found that the reaction of 2-(2-acyloxymethylphenyl)-2-alkoxy(or hydroxy)iminoacetamide with an amine is an industrially advantageous process for producing a 2-(2-hydroxymethylphenyl)-2-alkoxy(or hydroxy)iminoacetamide derivative useful as an intermediate for the production of alkoxyiminoacetamide compounds. After further studies based on this finding, the present invention has been completed.
That is, the present invention relates to: ##STR3## wherein R is hydrogen or an alkyl group, and R.sup.3 and R.sup.4 are the same or different and are hydrogen or an alkyl group, which comprises reacting a compound of the formula (II): ##STR4## wherein R.sup.1 is an optionally substituted alkyl group or an optionally substituted phenyl group, .about. indicates any configuration of an E-isomer, a Z-isomer and a mixture thereof, and the other symbols are as defined above, with a compound of the formula (III): ##STR5## wherein R.sup.2 is an alkyl group, and R.sup.3 and R.sup.4 are the same or different and are hydrogen or an alkyl group, which comprises reacting a compound of the formula (II-1): substituted phenyl group, .about. indicates any configuration of an E-isomer, a Z-isomer and a mixture thereof, and the other symbols are as defined above, with a compound of the formula (III): (I-1): ##STR6## wherein each symbol is as defined above, and then alkylating the compound of the formula (I-1); ##STR7## wherein R.sup.2 is an alkyl group, and R.sup.3 and R.sup.4 are the same or different and are hydrogen or an alkyl group, which comprises alkylating a compound of the formula (II-1): ##STR8## wherein R.sup.1 is an optionally substituted alkyl group or an optionally substituted phenyl group, .about. indicates any configuration of an E-isomer, a Z-isomer and a mixture thereof, and the other symbols are as defined above, to obtain a compound of the formula (II-2): ##STR9## wherein each symbol is as defined above, and then reacting the compound of the formula (II-2) with a compound of the formula (III): formula (II) is obtained by reacting a compound of the formula (VI): ##STR10## wherein R.sup.1 is as defined in above item (1), with a compound of the formula (V): formula (II-1) is obtained by reacting a compound of the formula (VI) with hydroxylamine and/or a salt thereof; formula (II-1) is obtained by reacting a compound of the formula (VI) with hydroxylamine and/or a salt thereof; compound of the formula (VI) is obtained by introducing a benzoyloxy group (in which the phenyl group may optionally be substituted) or an alkanoyloxy group (in which the alkyl group may optionally be substituted) into a compound of the formula (VII): ##STR11## wherein X is halogen; (8) The process according to above item (

REFERENCES:
patent: 5387714 (1995-02-01), Takase et al.
patent: 5442063 (1995-08-01), Takase et al.

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