Process for the preparation of insecticidal phenylhydrazine deri

Details Process for the preparation of insecticidal phenylhydrazine deri Process for the preparation of insecticidal phenylhydrazine deri

1999-11-01

2000-12-26

O'Sullivan, Peter

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

Organic compounds

Carboxylic acid esters

562 39, 564 34, 564101, 564137, 564141, 564143, 564144, 564310, 564314, C07C26904, C07C23102

Patent

active

061662437

ABSTRACT:
Disclosed herein is a method for making compounds having the structural formulae (I) or (II): ##STR1## wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C.sub.1 -C.sub.4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 haloalkanoyl dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C.sub.1 -C.sub.4 alkoxy carbonyl; and R is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C.sub.3 -C.sub.6 cycloalkyl; and Z is O or S, wherein the process comprises the steps of:
A) selecting as a starting material a compound of the structural formula ##STR2## B) reacting compound III with sodium nitrite in the presence of HCl to form the diazonium salt IV ##STR3## C) adding compound IV to freshly prepared alkali metal sulfite prepared by purging sulfur dioxide into an alkali metal hydroxide until the pH is between 7.3 and 7.5, thereby forming compound V ##STR4## D) reducing compound V with an alkali metal dithionite to form compound VI ##STR5## E) hydrolyzing compound VI under aid conditions to form compound VII ##STR6## and F) acylating compound VII to form compound I.

REFERENCES:
patent: 2547724 (1951-04-01), Sundholm
patent: 4725302 (1988-02-01), Ehrenfreund
patent: 5367093 (1994-11-01), Dekeyser et al.
patent: 5438123 (1995-08-01), Dekeyser et al.
Chemical Abstracts 105(17):152686c (1986).
Chemical Abstracts 108(19):163280d (1988).
DerWent Abstract 88-312695/44 (1988).
Chemical Abstract 126:86070 (1996).

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