Methods of producing sulfilimine compounds

1. A method of producing a sulfilimine compound, comprising:

reacting a sulfide compound with cyanamide, hypochlorite compound, and base to form a sulfilimine compound, wherein the sulfide compound has the following structure:

wherein:

X is a moiety selected from the group consisting of a halogen, a C 1 -C 4 alkyl, a C 1 -C 4 haloalkyl, a C 2 -C 4 alkenyl, a C 2 -C 4 alkynyl, a C 2 -C 4 haloalkenyl, a C 1 -C 4 alkoxy, a C 1 -C 4 haloalkoxy, CN, NO 2 , SO m R 6 where m is an integer from 0-2, COOR 4 , and CONR 4 R 5;

Y is a moiety selected from the group consisting of hydrogen, a halogen, a C 1 -C 4 alkyl, a C 1 -C 4 haloalkyl, a C 2 -C 4 alkenyl, a C 2 -C 4 alkynyl, a C 2 -C 4 haloalkenyl, a C 1 -C 4 alkoxy, a C 1 -C 4 haloalkoxy, CN, NO 2 , SO m R 1 where m is an integer from 0-2, COOR 4 , CONR 4 R 5 , aryl, and heteroaryl;

n is an integer from 0-3;

L is either a single bond, —CH(CH 2 ) p -where R 1 , S, and L taken together are a 4-, 5-, or 6-membered ring and p is an integer from 1-3, —CH(CH 2 OCH 2 )-where R 1 , S, and L taken together are a 6-membered ring, or —CH-where L, R 2 , and the common carbon to which they connect taken together are a 5-membered or 6-membered ring with up to, but no more than, 1 heteroatom;

R 1 is a moiety selected from the group consisting of a C 1 -C 4 alkyl, a C 1 -C 4 haloalkyl, a C 3 -C 6 alkenyl, a C 3 -C 6 alkynyl, a C 3 -C 6 haloalkenyl, an arylalkyl, a heteroarylalkyl, or —CH 2 — in cases where R 1 , S, and L taken together are a 4-, 5-, or 6-membered ring;

each of R 2 and R 3 is independently selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl, a C 1 -C 4 haloalkyl, a C 2 -C 4 alkenyl, a C 2 -C 4 alkynyl, a C 2 -C 4 haloalkenyl, a C 1 -C 4 alkoxy, a C 1 -C 4 haloalkoxy, CN, SO m R 6 where m is an integer from 0-2, COOR 4 , CONR 4 R 5 , an arylalkyl, a heteroarylalkyl, or R 2 and R 3 and the common carbon to which they attach form a 3-6 membered ring;

each of R 4 and R 5 is independently selected from the group consisting of hydrogen, a C 1 -C 4 alkyl, a C 1 -C 4 haloalkyl, a C 3 -C 6 alkenyl, a C 3 -C 6 alkynyl, a C 3 -C 6 haloalkenyl, an aryl, a heteroaryl, an arylalkyl, or a heteroarylalkyl; and

R 6 is a moiety selected from the group consisting of a C 1 -C 4 alkyl, a C 1 -C 4 haloalkyl, a C 3 -C 6 alkenyl, a C 3 -C 6 alkynyl, a C 3 -C 6 haloalkenyl, an arylalkyl, and a heteroarylalkyl.

2. The method of claim 1 , further comprising adding a buffer to the sulfide compound, cyanamide, hypochlorite compound, and base.

3. The method of claim 1 , wherein the base is selected from the group consisting of an alkali metal hydroxide, an alkali phosphate, an alkali metal carbonate, and combinations thereof.

4. The method of claim 1 , wherein reacting the sulfide compound with the cyanamide, hypochlorite compound, and base to form the sulfilimine compound is performed at a temperature from −40° C. to 30° C.

5. A method of producing a sulfilimine compound, comprising:

reacting cyanamide, hypochlorite compound, and base with a sulfide compound of the following formula:

wherein

each of R 7 and R 8 is independently selected from the group consisting of hydrogen, C 1 -C 4 alkyl, or either of R 7 or R 8 taken together with R 9 is a 4- to 6-membered saturated ring, and

R 9 is a C 1 -C 4 alkyl or R 9 taken together with either of R 7 or R 8 is a 4- to 6-membered saturated ring.

6. A method of producing a sulfilimine compound, comprising:

reacting 5-[1-(methylthio)ethyl]-2-trifluoromethylpyridine with cyanamide, sodium hypochlorite, and sodium carbonate to form a sulfilimine compound.