Process for manufacture of N-alkoxy(or aryloxy)carbonyl isothiocyanate derivatives in the presence of N,N-dialkylarylamine catalyst and aqueous solvent

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

• a) reacting a chloroformate compound of the general formula (I)
• wherein R1 represents a C1-C8 alkyl radical, a C2-C4 alkenyl radical, or a C6-C10 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 NH4,
• in the presence of an aqueous solvent, and in the presence of a catalytic amount of a N,N-dialkylarylamine of the general formula (II)
• wherein R2 each represents a C1-C8 alkyl radical or a C3-C6 alkenyl radical, or R2 together represent a C5 saturated heterocyclic ring or a C4 saturated heterocyclic ring wherein O may be part of the ring;
• and R3 represents an aryl group that can be a phenyl, a naphthyl, a substituted phenyl or a substituted naphthyl,
• to produce a N-alkoxy(or aryloxy)carbonyl isothiocyanate intermediate product of the general formula (IV)
• wherein R1 is as defined above in formula (I);
• and
• b) reacting the intermediate product (IV) with a compound of the general formula (V)
• R4—Y—H (V)
• wherein R4 represents a C1-C10 alkyl radical, a C6-C10 aryl radical or a C1-C8 alkoxy radical, and Y represents oxygen, sulfur, or NR5, wherein R5 represents hydrogen or R4,
• to produce a N-alkoxy(or aryloxy)carbonyl isothiocyanate derivative of the general formula (VI)
• wherein R1 is as defined above in formula (I), and R4 and Y are as defined above in formula (V).