N-alkylated thiazolium salts and process for their preparation

Process for preparing compounds of the formula (IIIb)

• 17
• where
• R2 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl and
• R3 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl or
• R2 and R3 together represent the following groups
• 18
• where the arrows indicate the linking points with the thiazole ring, or R2 and R3 together are radicals which are selected from the group of 1,3-propanediyl, 1,4-butanediyl or 1,5-pentanediyl, and the groups and radicals mentioned are optionally mono- or polysubstituted by halogen, nitro, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy and
• Y2 is iodine, bromine or chlorine and
• X is chlorine, bromine or iodine,
• comprising reacting compounds of the formula (III)
• 19
• where
• R1, R2 and R3 are each as defined under formula (I) and X is as defined under formula (II)
• with halides of the formula (IV)
• M(Y2)n (IV)
• where
• M is a metal ion having a valency n or a tertiary ammonium ion and
• Y2 is as defined under formula (IIIb).

Process for preparing compounds of the formula (IIIc)

• 20
• where
• R2 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl and
• R3 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl or
• R2 and R3 together represent the following groups
• 21
• where the arrows indicate the linking points with the thiazole ring, or R2 and R3 together are radicals which are selected from the group of 1,3-propanediyl, 1,4-butanediyl or 1,5-pentanediyl, and the groups and radicals mentioned are optionally mono- or polysubstituted by halogen, nitro, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy and
• Y3 is chlorine, bromine or iodine and
• (anion1)− is an anion of an acid or of a sulphonic acid, comprising effecting an anion exchange.

Thiazolium salts of the formula (IIId)

• 22
• where
• R2 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl and
• R3 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl or
• R2 and R3 together represent the following groups
• 23
• where the arrows indicate the linking points with the thiazole ring, or R2 and R3 together are radicals which are selected from the group of 1,3-propanediyl, 1,4-butanediyl or 1,5-pentanediyl, and the groups and radicals mentioned are optionally mono- or polysubstituted by halogen, nitro, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy and
• Y3 is chlorine, bromine or iodine and,
• in the case that
• Y3 is chlorine or bromine,
• R1 is primary or secondary C4-C12-alkyl and,
• in the case that
• Y3 is iodine
• R1 is primary or secondary C1-C3-alkyl, primary or secondary C4-C12-alkyl or C5-C15-arylalkyl and
• (anion2)− is an anion of an inorganic acid or of a sulphonic acid.

Compounds of the formula (VIb)

• 26
• where
• R2 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl and
• R3 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl or
• R2 and R3 together represent the following groups
• 27
• where the arrows indicate the linking points with the thiazole ring, or R2 and R3 together are radicals which are selected from the group of 1,3-propanediyl, 1,4-butanediyl or 1,5-pentanediyl, and the groups and radicals mentioned are optionally mono- or polysubstituted by halogen, nitro, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy and
• (anion3)− has the same definition and areas of preference as specified above.

Thiazoles of the formula (Ib)

• 28
• where
• R2 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl and
• R3 is hydrogen, C1-C12-alkyl, C4-C14-aryl or C5-C15-arylalkyl or
• R2 and R3 together represent the following groups
• 29
• where the arrows indicate the linking points with the thiazole ring, or R2 and R3 together are radicals which are selected from the group of 1,3-propanediyl, 1,4-butanediyl or 1,5-pentanediyl, and the groups and radicals mentioned are optionally mono- or polysubstituted by halogen, nitro, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy.