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US 2026/0250240 A1Published application
Photochemical systems and methods for preparing cyanobenzamides
AssigneesFMC Corporation, Fmc IP Technology GmbH
InventorsJianhua MAO, Hao WANG, Yihui XU
Life of this patent
Estimating the term…
Abstract
Described herein is a loop reactor system for performing photochemical reactions. The loop reactor system is particularly advantageous for preparing cyanobenzamides. Also disclosed are photochemical methods for preparing cyanobenzamides and compositions containing cyanobenzamides using.
Claims20
A method of preparing a compound of Formula II
- wherein:
- R12 and R13 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, and isomers thereof;
- R14 is selected from the group of amines, amides, carbamides, NH2, NR17R18, and NR21COR22;
- R15 is selected from the group of amides, C(O)NR19R20, and C(O)NHCH3;
- R16, R17, R18, R19, R20, R21, and R22 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, and isomers thereof;
- and
- Y is selected from the group of cyano-containing substituents and CN,
- the method comprising:
- I) forming a mixture comprising:
- a) a compound of Formula I
- wherein:
- R1 and R2 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl and isomers;
- R3 is selected from the group of amines, amides, carbamides, NH2, NR6R7, and NR8COR9;
- R4 is selected from the group of amides, C(O)NR10R11, and C(O)NHCH3;
- R5, R6, R7, R8, R9, R10, and R11 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, and substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl and isomers;
- and
- X is selected from the group of leaving groups, trifluoromethanesulfonate (TfO), tosylate (TsO), p-tosylate (p-TsO), mesylate (MsO), diethyl phosphate (PO4Et2), sulfonates (—OSO2R23), carboxylates (—OCOR24), diazonium, halogens, fluoride, chloride, bromide, and iodide;
- R23 and R24 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1-C6 haloalkyl, and C1-C6 fluoroalkyl;
- b) a cyano-containing compound;
- and
- c) optionally a solvent;
- and
- II) subjecting the mixture to irradiation from at least one light source.
20 more elements
A composition comprising:
- (a) a compound of Formula II
- wherein:
- R12 and R13 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, and isomers thereof;
- R14 is selected from the group of amines, amides, carbamides, NH2, NR17R18, and NR21COR22;
- R15 is selected from the group of amides, C(O)NR19R20, and C(O)NHCH3;
- R16, R17, R18, R19, R20, R21, and R22 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, and isomers thereof;
- and
- Y is selected from the group of cyano-containing substituents and CN,
- and
- (b) a compound of Formula I
- wherein:
- R1 and R2 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl and isomers;
- R3 is selected from the group of amines, amides, carbamides, NH2, NR6R7, and NR8COR9;
- R4 is selected from the group of amides, C(O)NR10R11, and C(O)NHCH3;
- R5, R6, R7, R8, R9, R10, and R11 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, and substituted or unsubstituted C3-C6 branched alkyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, and isomers thereof;
- and
- X is selected from the group of leaving groups, trifluoromethanesulfonate (TfO), tosylate (TsO), p-tosylate (p-TsO), mesylate (MsO), diethyl phosphate (PO4Et2), sulfonates (—OSO2R23), carboxylates (—OCOR24), diazonium, halogens, fluoride, chloride, bromide, and iodide;
- and
- R23 and R24 are each individually selected from the group of hydrogen, substituted or unsubstituted linear alkyl, substituted or unsubstituted C1-C6 linear alkyl, substituted or unsubstituted branched alkyl, substituted or unsubstituted C3-C6 branched alkyl, C1-C6 haloalkyl, and C1-C6 fluoroalkyl.
16 more elements
Dependencies are inferred from the claim text.