Process for the production of cyanine dyes

Details Process for the production of cyanine dyes Process for the production of cyanine dyes

1996-03-13

1999-12-28

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544301, 546102, 548455, 549 13, 549428, C09B 2312, C09B 2301, C07D40308

Patent

active

060083506

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to a process for the production of cyanine dyes with their methine chain showing the group (M) ##STR2## and the charge compensation occurring by linked end groups through transformation of cationic cyanine dyes comprising the following group (D) ##STR3## with CH-acid compounds of the formula I temperature ranging from 0 to 120.degree. C., the substituents having the following significance: possibly substituted once or twice by alkyl and/or aryl at the nitrogen atom, ##STR4## together the residue ##STR5## , wherein B.sub.3 represents the non-metal atoms and possibly their substituents necessary to close a carbo- or heterocyclic 5- to 7-membered ring. dialkyl-, diaryl- or alkylarylamino, nitro, cyano, alkyl- or arylsulphonyl, heterocyclyl or a residue of the formula L-S-, thiocarbonyl or iminocarbonyl, aryl, alkoxycarbonyl or together represent the non-metal atoms necessary to close a substituted or unsubstituted carbo- or heterocyclic 5- to 7-membered ring.
Preferred heteroaryl residues B.sub.2 have 5 or 6 ring members and 1 to 3 heteroatoms, such as O, S or N, especially substituted or unsubstituted 2-benzimidazolyl, 2-benzothiazolyl, 2-benzoxazolyl, 1,3,4-thiadiazol-2-yl, 1,2,4-triazol-3-yl, 2- or 4-pyridinyl or -quinolinyl.
In a preferred embodiment the group L is alkyl with 1 to 18 C-atoms, phenyl or naphthyl possibly substituted by chlorine, bromine, C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.18 -alkoxy, carboxyl or C.sub.1 -C.sub.18 -alkoxycarbonyl, heterocyclyl with 5 or 6 ring members and 1 to 3 heteroatoms, such as O, S or N, especially substituted or unsubstituted benzimidazol-2-yl, benzothiazol-2-yl, 2-pyridinyl, 4-pyridinyl, 1,2,4-triazol-3-yl or a 1,3,4-thiadiazol-2-yl residue, cyano, C.sub.1 -C.sub.18 -alkylcarbonyl, a residue of the formula ##STR6## wherein R.sub.110 represents C.sub.1 -C.sub.18 -alkoxy or di-(C.sub.1 -C.sub.10 -alkyl)-amino ##STR7## wherein R.sub.111 represents C.sub.1 -C.sub.18 -alkyl or aryl, ##STR8## wherein R.sub.112, R.sub.113 represent, independently of each other, H, C.sub.1 -C.sub.10 -alkyl, substituted or unsubstituted amino, aryl, or together represent the non-metal atoms necessary to close a 5- or 6-membered ring.
Heterocyclyl residues Q have preferably 5 to 7 ring members and 1 to 4 heteroatoms, the link to the methine chain of group D occurring over a C- or N-atom, especially residues of the 2-, 3- or 4-pyridinyl, 2-pyrazinyl, 3- or 4-pyridazinyl, 2-, 4- or 5-pyriminidyl, 2-, 3- or 4-pyranyl, 2-, 3- or 4-thiopyranyl, 2- or 3-pyrrolyl, 2- or 3-furanyl, thiophen-2- or -3-yl, 2-imidazolyl, 2-oxazolyl, 2-thiazolyl, 3-pyrazolyl, 3- or 5-isoxazolyl, 3- or 5-isothiazolyl, 1,3,4-thiadiazol-2-yl, 1,3,4-oxadiazol-2-yl or 1,2,4-triazol-3-yl series being linked to the methine chain over C-atoms, which residues of said heterocyclic series may carry fused-on rings, especially fused-on benzo-, naphtho- or cycloalkyl rings, and may further be substituted, especially by hydroxy, oxo, thioxo, ether, thioether, alkyl, aryl, cyano, nitro, carboxylic acid, ester or carbonamide groups or halogen, especially chlorine, bromine, fluorine. Further appropriate heterocyclic residues Q are pyrroles chain-linked over N-atoms, pyrazoles, imidazoles, triazoles, tetrazoles, pyrrolidines, morpholines, piperidines or piperazines each of which may be substituted by alkyl, aryl, heterocyclyl, acyl or alkoxycarbonyl residues, or imides or lactams chain-linked over N-atoms, especially N-phthalimidyl, N-succinimidyl, N-maleinimidyl, pyrrolidin-2-on-1-yl, caprolactam-1-yl.
In the process according to the present invention heterocyclyl residues Q for which the link to the methine chain occurs over an N-atom are preferred.
In the framework of the present invention the residues are preferably the following, unless stated explicitly otherwise: Alkyl residues include in addition to open-chain alkyl residues also cycloalkyl residues.
Open-chain alkyl residues contain 1 to 18 C-atoms and may also be branched, contain double or triple bonds and be interrupted

REFERENCES:
patent: 2715623 (1955-08-01), Fry et al.

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