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US 2023/0105595 A1Published application
Process of preparing 2-(phenylimino)-3-alkyl-1,3-thiazolidin-4-ones
AssigneeBayer Aktiengesellschaft
InventorsThomas HIMMLER, Sergii PAZENOK, Julia Johanna HAHN, Klaus-Ulrich SCHIFFER
Life of this patent
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Abstract
The present invention relates to a method for preparing 2-(phenylimino)-3-alkyl-1,3-thiazolidin-4-ones of the general formula (I) in which Y1, Y2, R1, R2 and R3 are as defined in the description.
Claims32
A method for preparing 2-(phenylimino)-3-alkyl-1,3-thiazolidin-4-one of formula (I)
- in which
- Y1 and Y2 are each independently fluorine, chlorine or hydrogen,
- R1 and R2 are each independently hydrogen, (C1-C12)alkyl, (C1-C12)haloalkyl, cyano, halogen or nitro, and
- R3 is optionally substituted (C6-C10)aryl, (C1-C12)alkyl or (C1-C12)haloalkyl, in which the substituents are selected from halogen, (C1-C6)alkyl, (C3-C10)cycloalkyl, cyano, nitro, hydroxy, (C1-C6)alkoxy, (C1-C6)haloalkyl and (C1-C6)haloalkoxy,
- Comprising reacting a 2-(phenylimino)-3H-1,3-thiazolidin-4-one of formula (VIII)
- in which Y1, Y2, R1 and R2 are as defined above,
- with an alkylating agent of formula (IX)
- R3—Z (IX)
- in which R3 is as stated above and
- Z is OSO2F
- in the presence of a base and a solvent.
8 more elements
A compound of formula (VIII)
- in which
- Y1 and Y2 are each independently fluorine, chlorine or hydrogen,
- R1 and R2 are each independently hydrogen, (C1-C12)alkyl, (C1-C12)haloalkyl, cyano, halogen or nitro.
A compound of formula (XII)
- in which
- Y1 and Y2 are each independently fluorine, chlorine or hydrogen,
- R1 and R2 are each independently hydrogen, (C1-C12)alkyl, (C1-C12)haloalkyl, cyano, halogen or nitro.
A compound of formula (XIV)
- in which
- Y1 and Y2 are each independently fluorine, chlorine or hydrogen,
- R1 and R2 are each independently hydrogen, (C1-C12)alkyl, (C1-C12)haloalkyl, cyano, halogen or nitro
- and R4 is methyl, ethyl or isopropyl.
1 more element
A compound of formula (XV)
- in which
- Y1 and Y2 are each independently fluorine, chlorine or hydrogen,
- R1 and R2 are each independently hydrogen, (C1-C12)alkyl, (C1-C12)haloalkyl, cyano, halogen or nitro;
- and Hal is chlorine or bromine.
1 more element
A compound of formula (VIII′)
- in which
- Y1 and Y2 are each independently fluorine, chlorine or hydrogen,
- R1 and R2 are each independently hydrogen, (C1-C12)alkyl, (C1-C12)haloalkyl, cyano, halogen or nitro.
A compound of formula (X)
- in which
- Y1 and Y2 are each independently fluorine, chlorine or hydrogen,
- R1 and R2 are each independently hydrogen, (C1-C12)alkyl, (C1-C12)haloalkyl, cyano, halogen or nitro,
- R3 is optionally substituted (C6-C10)aryl, (C1-C12)alkyl or (C1-C12)haloalkyl, in which the substituents are selected from halogen, (C1-C6)alkyl, (C3-C10)cycloalkyl, cyano, nitro, hydroxy, (C1-C6)alkoxy, (C1-C6)haloalkyl and (C1-C6)haloalkoxy.
1 more element
Dependencies are inferred from the claim text.