2
31
SYNTHESIS OF AMPHIPHILIC THIATRIMETHINECYANINES
succession with Et O and MeCN. The residue was
recrystallized from MeCN. Yields obtained under
The study was carried out under financial support of
the Russian Foundation for Basic Researc (grant 02-
2
optimum conditions (at 150°C), melting points, and 03-33336) NOW grant 047.009.019.
elemental analyses of benzothiazolium salts IVaIVc are
given in Table 2, H NMR spectra in Table 3.
1
REFERENCES
By evaporation in a vacuum of acetonitrile filtrate a
substance was separated containing according to the H
NMR spectrum predominantly 2-methyl-5-chlorobenzo-
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1
thiazole p-chlorobenzenesulfonate V with a little of salt
2
3
4
. Tyutyulkov, N., Fabian, J., Mehlhorn, F., Dietz, F., and Tad-
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1
IV as impurity. H NMR spectrum of compound V: 3.11 s
6
(
3H, Me), 7.28 d (2H, Harom, J 7.5 Hz), 7.50 d.d (1H, H ,
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J 8, J 1 Hz), 7.75 d (2H, Harom, J 7.5 Hz), 7.84 d (1H,
1
7
2
. Markov, R.V., Plekhanov,A.I., Rautian, S.G., Safonov, V.P.,
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4
H , J 8 Hz), 8.13 d (1H, H , J 1 Hz), 12.40 br.s (1H,
NH).
Preparation of 2-[3-(3-alkyl-5-chloro-2(3H)-
benzothiazolidene)-2-aryl-1-propenyl]-3-alkyl-5-
chlorobenzothiazolium iodides (IaIi). A mixture of
mmol of the respective benzothiazolium salt IVa
IVc, 6 mmol of trimethyl orthobenzoate, ortho(p-chloro-
benzoate) or ortho(p-fluorobenzoate) VIIIaVIIIc, and
5
6
. Avdeeva, V.I. and Shapiro, B.I., Zh. Nauchn. i Prikl.
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2
2
ml of pyridine (dried over KOHand distilled) was boiled
for 1.5 h. The reaction mixture was cooled, poured into
20% water solution of KI, and extracted with CH Cl .
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~
2
2
The extract was washed with 2% HCl and with water,
and dried with CaCl2. The solvent was distilled off in a
vacuum. The residue was two-fold subjected to
chromatography on a column packed with Al O ,
(
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9. Hada, H., Hanawa, R., Haraguchi, A., and Yonezawa, Y.,
2
3
J. Phys. Chem., 1985, vol. 89, p. 560.
collecting a violet fraction of dye (eluent CH Cl MeCN,
2
2
1
0.Shelkovnikov, V.V., Ivanova, Z.M., Orlova, N.A.,
Gerasimova, T.N., and Plekhanov,A.I., Opt. i Spektr., 2002,
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4
:1). The solution was evaporated, the residue was
dissolved in CH Cl and precipitated with Et O. The
2
2
2
relatively less stable dyes If, Ig were prepared by boiling
for 45 min and were subjected only once to chromato-
graphy.
1
1. Formina, L.V. and Lyubich, M.S., Tekhnologiya
registriruyushchikh sred (Technology of Registering
Media), 1989, p. 46.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 40 No. 2 2004