SU958452A1 - Process for producing monocarbocyanine dyes - Google Patents

Description

rametlinindolene-iodide) generally, but leads to the formation of the corresponding dye, whereby this method has found almost no use.

The purpose of the invention is to increase the yield of the target product.

This goal is achieved according to the method for producing monocarbocyanine dyes, consisting in the condensation of quaternary salts of heterocyclic bases containing the active methyl group derived from carboxylic KHCJJOTH when heated in an organic solvent in the presence of a basic catalyst. methyl group, use the compound of General formula (I-)

(I)

X

Where

R - CH 5,,

As a carboxylic acid derivative, an equimolar mixture of a carboxylic acid amide of the general formula (i)

ABOUT

C

(ABOUT)

 l

Nr

RO

H.W.XH, CHj,, (CH3) Cs, CPs, CZE ,;

R N, CH ,,, RI-H, CHj,

and phosphorus oxychloride. Dimethylformamide, acetic anhydride, pyridine can be used as a solvent.

The method is carried out as follows.

Example 1. 3,3-diethylthiacarbocyanine iodide.

0.54 ml of phosphorus oxychloride and then 1.5 g of 2-methyl-3-ethylbenzthiazolium iodide and 1.6 ml of triethylamine are added to 5. ml of dimethylformamide. The mixture is heated at boiling for 1 h., After cooling, 20 ml of water is added, the dye is filtered , washed with water, ether. Obtain 1.07 g (87%) of the dye, t.lp . .268 ° С X dks. 557 them (alcohol).

PRI mme R 2. 1, G-diethyl2-hinokarbotsianiniododu, Obtained analogously to example 1. Using 2-methyl-1-ethyl5 {inlinium iodide. Output 92%, so pl. 285-286 With,

max 605 m. (alcohol).

Primerz, 1,1-DIZTIL-4-HInocarbocyanine aniodide. Prepared analogously to example 1 using 4-methyl-1-ethyl-quinolinium iodide.

0 Yield 45%, mp. 249-251 C, 703 nm (alcohol) ...

PRI me R 4. 1,1,3,3,3,3-hexamethylindocarbocyanine iodide. Prepared analogously to example 1 using 1,2,3,3-tetramethylindolenium. Yield 40%, mp. 255-257 ° С, -max543 nm.

Note 5. 3,3-Diethyl-9-methylthiacarbocyanine aniodide. To suspension

f. 0.34 g of acetanilide in 2 ml of acetic anhydride was added 0.46 g of phosphorus oxychloride and stirred until complete dissolution, after which 2 ml of acetic anhydride, 1 ml of pyridine, 1.5 g-methyl-3-ethylbenzthiazolium iodide and 0, 5 ml of triethylamine. The mixture is boiled for 30 minutes at the boil, cooled, the precipitate is filtered off and washed with water, ether. Get

Q 0.65 g (52%) dye, so pl. 275277 ° C, L "AC; with 542 nm (alcohol).

PRI me R 6. 3,3, 9-triethylthiacarbocyanine aniodide. Prepared analogously to example 5, using amide

with propionic acid. Yield 40%, mp.

238-240 ° C, Hmaks. 547 nm (alcohol).

PRI me R 7. 3 3-diethyl-9-phenylthiacarbacyanide

Prepared analogously to example 5 using benzoic acid amide. Yield 42%, mp. .274-276 0, max 560 nm (alcohol).

PRI me R 8. 3,3-diethyl-9-tert. butylthiacarbocyaninide. Prepared analogously to example 5 using

5 amide of pivalic acid. Yield 44%

m.p. 227-2280c, 564 nm (alcohol).

PRI me R 9. 3,3-diethyl-9 trifluoromethylthiacarbocyanine iodide. Prepared analogously to example 5 using trifluoroacetic acid amide. Yield 35%, mp. 256-257 ° C, max 580 nm (alcohol). ,

Example 10. 3,3-diethyl-9-per55 fluoropropyl thiacarbocyanine iodide.

Claims (2)

Prepared analogously to Example 5 using perfluorobutyric acid amide. Yield 33%, mp. 218-220 C, 590 nm (alcohol). 0 The use of the proposed method for producing monocarbocyanine dyes provides, in comparison with the known method, an increase in the yield of the target products, an expansion of the range of dyes. For example, a dye (Example 1) according to the prototype is formed with a yield of 64%, according to the proposed method with a yield of 87%. For dye (example 2, this comparison looks as follows: 10% (according to the prototype) and 92% (according to the proposed method), for dye (example 4) - O (according to the prototype) and 40% (according to the proposed method). Dyes ( Examples 5-10) The method of the invention cannot be obtained according to the known method. 1. A method of producing monocarbocyanine dyes by condensing the quaternary salts of heterocyclic bases containing the active methyl group with a carboxylic acid derivative when heated in an organic solvent in the presence of a basic catalytic acid. pa, characterized in that, in order to increase the yield of the target product, as the quaternary salts of heterocyclic bases containing the active methyl group, an equimolar mixture of the general formhla (I) R CH3, C-jHsf is used as a carboxylic acid derivative carboxylic acid amide of the general formula (m) 6 (P) / where X HiCH3 ,,, CF, CjF-, R -1 - H CH j, RH, CHjiH phosphorus oxychloride. 2. Method according to Claim 1, about t and tea and with the fact that dimethylformamide, acetic anhydride or pyridine is used as an organic solvent. Information sources, . taken into account in the examination 1. German patent 731898, cl. 22 e 3, pub. 1931. 2. Patent IT 2487881, cl. 26G-240..65, published. 1949- (prototype).