http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-2561355-T3

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filingDate 2007-02-09-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2016-02-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_d957998cfb27184bfc3a5c7a6102ccc1
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publicationDate 2016-02-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber ES-2561355-T3
titleOfInvention Procedure for the oxidation of certain sulfilimines substituted to insecticidal sulfoximins
abstract A process for the preparation of sulfoximins (Ia) insecticides, ** Formula ** in which Het represents ** Formula ** X represents halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl , C2-C4 haloalkenyl, C1-C4 alkoxy, C1-C4 haloalkoxy, CN, NO2, SOmR6 wherein m is an integer from 0-2, COOR4 or CONR4R5; 10 Y represents hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C2-C4 haloalkenyl, C1-C4 alkoxy, C1-C4 haloalkoxy, CN, NO2, SOmR1 in which m is an integer of 0-2, COOR4 or CONR4R5, aryl or heteroaryl; n is an integer from 0-3; L represents a single bond, -CH (CH2) p- in which R1, S and L taken together represent a 4, 5 or 6-membered ring and p is an integer of 1-3, -CH (CH2OCH2) - in which R1, S and L taken together represent a 6-membered ring, or -CH- in which L, R2 and the common carbon to which they are connected together represent a 4, 5 or 6-membered ring with up to, but no more than, 1 heteroatom. R1 represents C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 haloalkenyl, arylalkyl, heteroarylalkyl, or -CH2- in cases where R1, S and L taken together represent a ring of 4, 5 or 6 members. R2 and R3 independently represent hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C2-C4 haloalkenyl, C1-C4 alkoxy, C1-C4 haloalkoxy, CN, SOmR6 in which m is an integer of 0-2, COOR4 or CONR4R5, arylalkyl, heteroarylalkyl, or R2 and R3 and the common carbon to which they are attached form a 3-6 membered ring; R4 and R5 independently represent hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 haloalkenyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl; and R6 represents C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 haloalkenyl, arylalkyl or heteroarylalkyl; and wherein "alkyl", "alkenyl", "alkynyl" and "alkoxy" include straight chain, branched and cyclic chain moieties, and each may be unsubstituted or substituted with one or more substituents selected from, but not limited to a, halogen, hydroxy, alkoxy, alkylthio, C1-C6 acyl, formyl, cyano, aryloxy or aryl, provided that the substituents are sterically compatible and the chemical bond and deformation energy rules are met; and "aryl" refers to a phenyl, indanyl or naphthyl group; and "aryl" and "heteroaryl" may be unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, nitro, cyano, aryloxy, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1 alkoxy -C6, halogenated C1-C6 alkyl, halogenated C1-C6 alkoxy, C1-C6 acyl, C1-C6 alkyl, (C1-C6 alkyl) -sulfinyl, (C1-C6 alkyl) -sulfonyl, aryl, (C1-C6 alkyl ) -OC (O), (C1-C6 alkyl) -NHC (O), C (O) OH, (C1-C6 alkyl) - C (O) O, C (O) NH2, (C1-C6 alkyl) -C (O) NH or (C1-C6 alkyl) 2-C (O) N, as long as the substituents are sterically compatible and the chemical bond and deformation energy rules are met; which comprises oxidizing a sulfilimine of formula (I) ** Formula ** in which R1, R2, R3, L, Het and n are as previously defined by contacting sulfilimine in an appropriate organic solvent that is essentially inert in the strong oxidizing conditions with an oxidizing agent comprising an alkali metal permanganate at a temperature of -10 to 45 ° C.
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