2-(substituted imino)-1,3,4-dihydrothiadiazoles
AssigneeICI Americas Inc.
InventorRaymond A. Felix
Life of this patent
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Abstract
This invention relates to a process for producing a compound of the formula ##STR1## comprising reacting a compound having the formula ##STR2## with cyanogen chloride or cyanogen bromide.
Claims3
A process for producing a compound of the formula ##STR64## in which R is halo, trihalomethyl, pentahaloethyl, mono- or difluoromethyl, mono-, di-, tri- or tetrafluoroethyl, fluoroalkylthio, fluoroalkoxy, methylthio, methylsulfonyl, halomethylsulfonyl, C.sub.1 -C.sub.2 alkyl, or methoxy;
- n is 1 or 2, provided that:
- (a) is n is 1 and R is other than fluoro, the substituent R is located at the 3-position on the phenyl ring;
- and
- (b) if n is 2, the substituents R are located at the 3- and 4-positions on the phenyl ring;
- R.sub.1 is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 alkyl thio, C.sub.3 -C.sub.4 alkenylthio, cyano, carbamyl, C.sub.1 -C.sub.4 mono-alkylcarbamyl, C.sub.1 -C.sub.2 carboalkoxy, or NR.sub.3 R.sub.4 in which R.sub.3 and R.sub.4 are independently hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkenyl;
- and
- R.sub.2 is hydrogen, comprising reacting a compound having the formula ##STR65## with cyanogen chloride or cyanogen bromide.
A process for producing a compound of the formula ##STR67## in which R is halo, trihalomethyl, pentahaloethyl, mono- or difluoromethyl, mono-, di-, tri- or tetrafluoroethyl, fluoro alkylthio, fluoroalkoxy, methylthio, methylsulfonyl, halomethyl sulfonyl, C.sub.1 -C.sub.2 alkyl, or methoxy;
- n is 1 or 2, provided that:
- (a) is n is 1 and R is other than fluoro, the substituent R is located at the 3-position on the phenyl ring;
- and
- (b) if n is 2, the substituents R are located at the 3- and 4-positions on the phenyl ring;
- R.sub.1 is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 alkenylthio, cyano, carbamyl, C.sub.1 -C.sub.4 mono-alkylcarbamyl, C.sub.1 -C.sub.2 carboalkoxy, or NR.sub.3 R.sub.4 in which R.sub.3 and R.sub.4 are independently hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkenyl;
- and
- R.sub.2 is C.sub.1 -C.sub.4 mono- or dialkylcarbamyl;
- phenylcarbamyl;
- C.sub.1 -C.sub.4 mono-alkylthiocarbamyl;
- C.sub.4 -C.sub.6 ketoalkenyl;
- cyano;
- C.sub.1 -C.sub.4 alkylsulfonyl;
- C.sub.1 -C.sub.4 haloalkylsulfonyl;
- or ##STR68## in which Y is oxygen or sulfur;
- m is 0 or 1;
- and R.sub.5 is C.sub.1 -C.sub.10 alkyl;
- C.sub.2 -C.sub.10 alkenyl;
- C.sub.2 -C.sub.8 alkynyl if m is 0;
- C.sub.3 -C.sub.8 alkynyl in which the triple bond is separated from the oxygen or sulfur atom (Y) by at least one methylene group if m is 1;
- C.sub.1 -C.sub.8 haloalkyl if m is 0;
- C.sub.2 -C.sub.8 haloalkyl if m is 1;
- C.sub.2 -C.sub.10 alkoxyalkyl if m is 0;
- pyridyl if m is 0;
- C.sub.3 -C.sub.10 alkoxyalkyl in which the alkylene portion has at least two carbon atoms if m is 1;
- or R.sub.5 is
- (R.sub.6).sub.p R.sub.7
- in which p is 0 or 1;
- R.sub.6 is a C.sub.1 -C.sub.2 alkylene group and R.sub.7 is phenyl, halo-substituted phenyl, C.sub.3 -C.sub.7 cycloalkyl, optionally substituted by from 1 to 3 methyl groups;
- C.sub.1 -C.sub.4 carboalkoxy;
- or a saturated or unsaturated heterocyclic ring containing from 5 to 6 atoms including from 1 to 2 hetero atoms selected from oxygen and sulfur, optionally substituted by from 1 to 3 methyl groups and optionally substituted by from 1 to 2 oxo groups;
- provided that when R.sub.1 is methylthio and R.sub.2 is isopropylcarboxy, then R is not 2-fluoro, comprising
- (a) reacting a compound having the formula ##STR69## with cyanogen chloride or cyanogen bromide, optionally in the presence of a base;
- and
- (b) reacting the product of step (a) with an acylating agent selected from the group consisting of compounds having the formula ##STR70## in which Z' is a halogen and isocyanates and isothiocyanates having the formula R.sub.9 --NCO or R.sub.9 NCS in which R.sub.9 is C.sub.1 -C.sub.4 alkyl or phenyl.
Dependencies are inferred from the claim text.