US 4,736,056 AGranted

Process for the production of malonic acid derivative compounds

OwnerOliver W. Smith, Russell J. Outcaltinventors

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Abstract

This invention relates to a process for preparing a malonic acid derivative compound of formula (i) depicted herein in high yield and high purity by reacting a malonic acid derivative compound of formula (ii) depicted herein with an alkylating agent of formula (iii) depicted herein in the presence of a solvent and a base.

Claims33

Dependent claims

A process for preparing a compound of formula (i) ##STR6## which comprises reacting a compound of formula (ii) ##STR7## with a compound of formula (iii)

X.sub.1 -Y.sub.4 -X.sub.2 (iii)
in the presence of a solvent and a base;
wherein:
R.sub.1 alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, acylalkyl, aroylalkyl, dialkoxyphosphinylalkyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, acylaminoalkyl, acyloxyalkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl;
R.sub.2 and R.sub.3 are the same or different and are halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonyl amino, acyloxy or alkenyl;
n is a value of from 0 to 4;
Y.sub.1 is O, S or N(alkyl);
Y.sub.2 and Y.sub.3 are independently oxygen or sulfur;
Y.sub.4 is a substituted or unsubstituted branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are the same or different and are one or more halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy or alkenyl, with the proviso that X.sub.1 and X.sub.2 are not directly bonded to a heteroatom;
and
X.sub.1 and X.sub.2 are independently nucleofuge groups having sufficient leaving capability to permit the reaction of a compound of formula (iii) with a compound of formula (ii) to form a compound of formula (i).

8 more elements

Dependencies are inferred from the claim text.

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Abstract

A process for preparing a compound of formula (i) ##STR6## which comprises reacting a compound of formula (ii) ##STR7## with a compound of formula (iii)

X.sub.1 -Y.sub.4 -X.sub.2 (iii)
in the presence of a solvent and a base;
wherein:
R.sub.1 alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, acylalkyl, aroylalkyl, dialkoxyphosphinylalkyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, acylaminoalkyl, acyloxyalkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl;
R.sub.2 and R.sub.3 are the same or different and are halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonyl amino, acyloxy or alkenyl;
n is a value of from 0 to 4;
Y.sub.1 is O, S or N(alkyl);
Y.sub.2 and Y.sub.3 are independently oxygen or sulfur;
Y.sub.4 is a substituted or unsubstituted branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are the same or different and are one or more halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy or alkenyl, with the proviso that X.sub.1 and X.sub.2 are not directly bonded to a heteroatom;
and
X.sub.1 and X.sub.2 are independently nucleofuge groups having sufficient leaving capability to permit the reaction of a compound of formula (iii) with a compound of formula (ii) to form a compound of formula (i).

8 more elements