Process for the preparation of benzonitrile compounds
AssigneeNissan Chemical Industries, Ltd.
InventorsYasuo Kondo, Yasuhisa Sugiyama, Norio Tanaka
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Abstract
A novel process for the preparation of benzonitrile compounds useful for herbicides or their intermediates is provided. A process for the preparation of compounds of the formula (1), characterized in comprising reacting a compound of the formula (1a) with one or more cyanides selected from potassium cyanide, sodium cyanide and zinc cyanide in the presence of a metallic catalyst. In the scheme, X is hydrogen, fluorine or chlorine atom; Z is nitro, amino or C1-C4 alkylsulfonylamino group or the like; Y is fluorine, chlorine or bromine atom or the like; and Q is hydrogen atom, or nitro or amino group or the like.
Claims16
A process for the preparation of benzonitrile compounds having the formula (1):
- wherein:
- X is hydrogen, fluorine or chlorine;
- Z is C1-C4 alkylsulfonylamino, bis (C1-C4 alkylsulfonyl)amino, (C2-C5 alkoxycarbonyl)amino, (C2-C5 alkylcarbonyl)amino, (optionally substituted benzoyl)amino, (C2-C5 alkylcarbonyl) (C1-C4 alkylsulfonyl)amino or (optionally substituted benzoyl) (C1-C4 alkylsulfonyl)amino;
- and
- Q is 6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione-3-yl, 1-methyl-6-trifluoromethyl-2,4(1H, 3H)pyrimidinedione-3-yl or 1-amino-6-trifluoromethyl-2,4(1H, 3H)pyrimidinedione-3-yl group, which process comprises reacting a halogenated benzene compound having the formula (1a):
- wherein X, Z and Q are as defined above;
- and Y is fluorine, chlorine, bromine or iodine;
- provided that if X is fluorine, then Y is chlorine, bromine or iodine;
- and if X is chlorine;
- then Y is bromine or iodine;
- with one or more cyanides selected from the group consisting of potassium cyanide, sodium cyanide and zinc cyanide in the presence of a metallic catalyst, comprising:
- iron, cobalt, nickel, ruthenium, rhodium, palladium, iridium, platinum, or osmium.
Dependencies are inferred from the claim text.