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Preparation method for bis(rhodanine)merocyanine sensitizing dye with a benzothiazole skeloton

A technology of benzothiazole and sensitizing dyes, applied in organic dyes, chemical instruments and methods, methine/polymethine dyes, etc., to achieve the effects of low environmental pollution, high product purity, and low cost

Inactive Publication Date: 2014-02-19
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are few reports on the synthesis of such related compounds in the literature at home and abroad.

Method used

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  • Preparation method for bis(rhodanine)merocyanine sensitizing dye with a benzothiazole skeloton
  • Preparation method for bis(rhodanine)merocyanine sensitizing dye with a benzothiazole skeloton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Add 14.9 g (0.1 mol) 2-methylbenzothiazole, 18.3 g (0.15 mol) 1,3-propane sultone, 100 mL toluene into a three-necked flask, and heat to reflux for 15 h. Cool, filter, and dry to obtain 14.9 g of solids, with a yield of 85%. 1 H NMR (400 MHz, D 2 O-d 2 ), δ : 7.64~8.07 (m, 4H, Ar—H), 4.77~4.78,(t, J =8.0 Hz, 2H, N—CH 2 ), 3.07 (s, 3H, —CH 3 ), 3.00~3.02 (t, J =6.0 Hz, 2H, CH 2 —S), 2.24~2.31 (m, 2H, —CH 2 —); MS (ESI), m / z : 272, 294.

[0026] (2) Add 13.5 g (0.05 mol) of 2-methyl-3-(3 ， -Propylsulfonate)benzothiazole, add 15 mL of cresol, raise the temperature to 120 °C, add 14.1 g (0.08 mol) triethyl orthopropionate dropwise, and continue the reaction for 2 h. After cooling, 100 mL of ethyl acetate was added to precipitate a solid, which was filtered and dried to obtain 13.1 g of a solid with a yield of 73.8%. m.p. above 300 ℃ (decomposition); 1 H NMR (400 MHz, CD 3 OD-d 4 ), δ : 7.63~8.15 (m, 4H, Ar—H), 6.68 (s, 1H, —CH=), 4.90~4.94,(t, J =8.0...

Embodiment 2

[0031] (1) Add 14.9 g (0.1 mol) 2-methylbenzothiazole, 20.4 g (0.15 mol) 1,4-butane sultone, and 100 mL chlorobenzene into a three-necked flask, and heat to reflux for 15 h. Cool, filter, and dry to obtain 23.1 g of solids, with a yield of 81%.

[0032] (2) Add 14.3 g (0.05 mol) of 2-methyl-3-(3 ， -Butylsulfonate)benzothiazole, add 15 mL of cresol, raise the temperature to 120 °C, add 16.2 g (0.1 mol) triethyl orthoacetate dropwise, and continue the reaction for 2 h. After cooling, 100 mL of ethyl acetate was added to precipitate a solid, which was filtered and dried to obtain 16.5 g of a solid with a yield of 93%.

[0033] (3) Add 17.7 g (0.05 mol) of 2-(2-ethoxy-1-propenyl)-1-(3-sulfonic acid butyl) benzothiazole and 13.1 g (0.06 mol) For rhodanine methyl propionate, 20 mL of absolute ethanol was added, the temperature was raised to reflux, 0.085 g (0.01 mol) of piperidine was added dropwise, and the reaction was continued for 2 h. Cool, evaporate methanol to dryness, add...

Embodiment 3

[0038] (1) Add 14.9 g (0.1 mol) 2-methylbenzothiazole, 18.3 g (0.15 mol) 1,3-propane sultone, 100 mL toluene into a three-necked flask, and heat to reflux for 15 h. Cool, filter, and dry to obtain 14.9 g of solids, with a yield of 85%.

[0039] (2) Add 14.3 g (0.05 mol) of 2-methyl-3-(3 ， -Propylsulfonate)benzothiazole, add 15 mL of cresol, raise the temperature to 120 °C, add 16.2 g (0.1 mol) trimethyl orthopropionate dropwise, and continue the reaction for 2 h. After cooling, 100 mL of ethyl acetate was added to precipitate a solid, which was filtered and dried to obtain 14.7 g of a solid with a yield of 90%.

[0040] (3) Add 16.5 g (0.05 mol) of 2-(2-methoxy-1-propenyl)-1-(3-sulfonic acid butyl) benzothiazole and 12.5 g (0.06 mol) Add 20 mL of absolute ethanol to rhodanine methyl acetate, heat up to reflux, add 0.075 g (0.01 mol) pyridine dropwise, and continue the reaction for 2 h. Cool, evaporate methanol to dryness, add 50 mL of acetone, and precipitate a solid. Filt...

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Abstract

The invention belongs to bis(rhodanine)merocyanine sensitizing dyes, belongs to the field of organic synthetic dyes, and especially relates to a preparation method of a bis(rhodanine)merocyanine sensitizing material by taking 2-methylbenzothiazole and a rhodanine derivative as main initial raw materials. The target product is obtained by taking low-price 2-methylbenzothiazole and rhodanine carboxylate as the raw materials and performing five-step reaction. The beneficial effects comprise that: the method is simple and easy in reaction operation, small in environmental pollution, high in product purity and relatively low in cost, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthetic dyes, and relates to a preparation method of biserodanine cyanine sensitizing dye by using 2-methylbenzothiazole and rhodanine carboxylic acid derivatives as main starting materials. Background technique [0002] Rhodanine cyanine sensitizing dye is a new type of photographic sensitizing dye, the general structural formula is: [0003] [0004] Among them, n 1 is 3 or 4, n 2 1~5, R 1 for -H, -Me, -Et, -Pr; R 3 for -COOH, -CO 2 Me,—CO 2 Et,—CO 2 Bu-t. [0005] With the rapid development of storage materials and information recording, cyanine dyes, as a spectral sensitizing dye, have been widely used in photosensitive materials. People use cyanine dyes to have the advantages of easy synthesis, low price, and good optical properties, making it more and more important in organic storage discs, photosensitive films, and fluorescent probes. [0006] Shuangluotanin cyanine sensitizing dye is ...

Claims

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Application Information

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IPC IPC(8): C07D277/64C09B23/04
CPCC07D277/64C09B23/04
Inventor 杨运旭霍宝龙薛灵伟
Owner UNIV OF SCI & TECH BEIJING
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