Process for manufacturing N-alkoxy(or aryloxy)carbonyl isothiocyanate derivatives using N,N-dialkylarylamine as catalyst

A process for the preparation of N-alkoxy(or aryloxy)carbonyl isothiocyanate derivatives comprising:

• a) reacting a haloformate compound of the general formula (I) ##STR9## wherein R.sup.1 represents a C.sub.1 -C.sub.8 alkyl radical or a C.sub.2 -C.sub.4 alkenyl radical, or a C.sub.6 -C.sub.10 aryl radical, and X represents a halogen atom,
• with a thiocyanate of the general formula (II)
• MSCN (II)
• wherein M represents an alkali or alkaline earth metal, lead or NH.sub.4,
• in the presence of an organic solvent and in the presence of a catalytic amount of a N,N-dialkylarylamine of the general formula (III) ##STR10## wherein R.sup.2 each represents a C.sub.1 -C.sub.8 alkyl radical or a C.sub.3 -C.sub.6 alkenyl radical, or R.sup.2 together represent a C.sub.5 saturated heterocyclic ring or a C.sub.4 saturated heterocyclic ring wherein O may be part of the ring;
• and R.sup.3 represents an aryl group which is selected from a phenyl, a naphthyl, a substituted phenyl and a substituted naphthyl,
• to produce a N-alkoxy(or aryloxy)carbonyl isothiocyanate intermediate product of the general formula (IV) ##STR11## wherein R.sup.1 is as defined above in formula (I);
• and b) reacting the intermediate product (IV) with a compound of the general formula (V)
• R.sup.4 --Y--H (V)
• wherein R.sup.4 represents a C.sub.1 -C.sub.10 alkyl radical, a C.sub.6 -C.sub.10 aryl radical or a C.sub.1 -C.sub.8 alkoxy radical, and Y represents oxygen, sulfur, or NR.sup.5, wherein R.sup.5 represents hydrogen or R.sup.4,
• to produce a N-alkoxy(or aryloxy)carbonyl isothiocyanate derivative of the general formula (VI) ##STR12## wherein R.sup.1 is as defined above in formula (I), and R.sup.4 and Y are as defined above in formula (V).