Patent ID: 6222045
Filing Date: 2001-04-24
Classification: C07D

Abstract:
A process for preparing a substituted triazolinone comprising steps of:a) reacting an isothiocyanate of the formula (I)R.sup.1 --N.dbd.C.dbd.S (I)whereinR.sup.1 represents an unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,with an alkanol of the formula (II)R.sup.2 --O--H (II)whereinR.sup.2 represents an unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,in the presence of a catalytic amount of base, to produce a thionocarbamate intermediate product of the formula (III) ##STR9##whereinR.sup.1 and R.sup.2 are as defined above; andb) reacting the intermediate product of formula (III) with an alkylating agent of the formula (IV)R.sup.3 --X (IV)whereinX represents a halogen, --O--SO.sub.2 --O--R.sup.3, or --O--CO--O--R.sup.3,R.sup.3 represents an unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,in the presence of a base, to produce an imino intermediate product of the formula (V) ##STR10##whereinR.sup.1, R.sup.2 and R.sup.3 are as defined above, andc) reacting the intermediate product of formula (V) with a compound of the formula (VI)H.sub.2 N--NH--CO.sub.2 --R.sup.4 (VI)whereinR.sup.4 represents an alkyl or an aryl,in the presence of a catalytic amount of an acid to produce a compound of the formula (VII) ##STR11##whereinR.sup.1, R.sup.2 and R.sup.4 are each as defined above; andd) reacting the product of the formula (VII) with a catalytic amount of a base to produce a substituted triazolinone of the formula (VIII) ##STR12##whereinR.sup.1 and R.sup.2 are each as defined above.