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Method for producing 2-hydrazinobenzothiazole derivative

A manufacturing method, -CH2- technology, applied to chemical instruments and methods, coatings, instruments, etc., can solve the problem that the separation yield of the target object is not necessarily sufficient, and achieve the reduction of difficult orientation, not easy to change color, and ensure transparency sexual effect

Active Publication Date: 2018-09-04
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the isolated yield of the target compound in the previous method may not be sufficient

Method used

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  • Method for producing 2-hydrazinobenzothiazole derivative
  • Method for producing 2-hydrazinobenzothiazole derivative
  • Method for producing 2-hydrazinobenzothiazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0141] (Example 1) Production of a compound represented by formula (C-1)

[0142] [chem 26]

[0143]

[0144] Under a nitrogen atmosphere, 2.00 g of the compound represented by the formula (C-1-1) and 20 mL of tetrahydrofuran were added to the reaction container. 1.49 g of potassium tert-butoxide was added under ice cooling, and stirred for 2 hours. A solution obtained by dissolving 2.82 g of the compound represented by the formula (C-1-2) in 3 mL of tetrahydrofuran was added dropwise. After stirring at room temperature for 5 hours, it was diluted with 100 mL of dichloromethane, and poured into water. The organic layer was washed with brine, dried over sodium sulfate, and the solvent was distilled off. It purified by column chromatography (silica gel, hexane / ethyl acetate (75:25)), and obtained 2.35 g of the compound represented by Formula (C-1). The yield from the compound represented by formula (C-1-1) was 78%. The reaction solution after the reaction exhibited light...

Embodiment 2

[0149] (Example 2) Production of a compound represented by formula (C-2)

[0150] [chem 28]

[0151]

[0152] Under a nitrogen atmosphere, 2.00 g of the compound represented by the formula (C-2-1) and 20 mL of tetrahydrofuran were added to the reaction container. 0.52 g of sodium amide was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. A solution obtained by dissolving 2.45 g of the compound represented by the formula (C-2-2) in 5 mL of tetrahydrofuran was added dropwise. After stirring at room temperature for 5 hours, it was diluted with 100 mL of dichloromethane, and poured into water. The organic layer was washed with brine, dried over sodium sulfate, and the solvent was distilled off. Column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / hexane) were performed to obtain 2.49 g of the compound represented by the formula (C-2). The yield from the compound represented by formula (C-2-1) was 93%...

Embodiment 3

[0157] (Example 3) Production of a compound represented by formula (C-3)

[0158] [chem 30]

[0159]

[0160] Under a nitrogen atmosphere, 2.00 g of the compound represented by the formula (C-3-1) and 20 mL of tetrahydrofuran were added to the reaction container. 0.69 g of sodium methoxide was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. A solution obtained by dissolving 3.17 g of the compound represented by the formula (C-3-2) in 5 mL of tetrahydrofuran was added dropwise. After stirring at room temperature for 5 hours, it was diluted with 100 mL of dichloromethane, and poured into water. The organic layer was washed with brine, dried over sodium sulfate, and the solvent was distilled off. Column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / hexane) gave 2.67 g of the compound represented by the formula (C-3). The yield from the compound represented by formula (C-3-1) was 80%. The reaction ...

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Abstract

The present invention provides a novel method for producing a 2-hydrazinobenzothiazole derivative. The present invention also provides: a method for producing a compound using the 2-hydrazinobenzothiazole derivative obtained by said production method; and a composition containing said compound. The present invention also provides a polymerizable composition which is useful for producing a film-like polymer and contains the compound obtained by said production method. The present invention provides: a method for producing a compound represented by general formula (I-C), the method comprising astep for reacting a compound represented by general formula (I-B) and a compound represented by general formula (I-A) in the presence of at least one compound selected from the group consisting of metal amides, metal hydrides, metal alkoxides and organic alkali metals; a compound derived from the compound produced by said production method; and a composition containing said compound.

Description

technical field [0001] The present invention relates to a method for producing a 2-hydrazinobenzothiazole derivative, a method for producing a compound using the 2-hydrazinobenzothiazole derivative, a polymerizable composition containing the compound, a polymerizable liquid crystal composition, and a method using the 2-hydrazinobenzothiazole derivative. An optically anisotropic body of the polymerizable liquid crystal composition. Background technique [0002] In order to increase the viewing angle of a liquid crystal display, it is necessary to reduce the wavelength dispersion of the birefringence of the retardation film or make it negative. As a material for this, various compounds having reverse wavelength dispersibility or low wavelength dispersibility have been developed. As such a compound, a compound having a hydrazone site and a benzothiazole site having a substituent such as an alkyl group introduced into the nitrogen atom is known. Examples of key intermediates i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/82C09K19/38G02B5/30G02F1/13363
CPCC07D277/82C09K19/38G02F1/13363G02B5/30C09K19/3497C09K2019/0448C09D4/00C08F2/50C08F122/24C08F120/38C08F22/14
Inventor 堀口雅弘间宫纯一
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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