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Preparation method of 2'-[bis (phenylmethyl) amino]-6'-(diethylamino)-spiro [isobenzofuran-1 (3H), 9'-[9H] xanthen]-3-one

A technology of diethylamino and phenylmethyl, which is applied in the field of pressure-sensitive dye preparation, can solve the problems of low yield, achieve the effect of increasing product yield, improving appearance characteristics and yield

Inactive Publication Date: 2013-06-12
连云港珂玫琳科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its defect is: this method uses concentrated sulfuric acid as reaction medium, has sulfonate production, and yield is also low

Method used

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  • Preparation method of 2'-[bis (phenylmethyl) amino]-6'-(diethylamino)-spiro [isobenzofuran-1 (3H), 9'-[9H] xanthen]-3-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1, a 2'-[(bis(phenylmethyl)amino]-6'-(diethylamino)-spiro(isobenzofuran-1(3H),9'-(9H)xanthene ) The preparation method of-3-ketone, its step is as follows:

[0014] (1) Add sodium hydroxide solution with a mass concentration of 30% to the reaction vessel, phase transfer catalyst tetrabutylammonium bromide, p-methoxyaniline, raise the temperature to 70°C, add benzyl chloride dropwise; then heat the reaction Heat the material to 90°C and keep it warm for 3 hours, then cool down to 80°C, add 80°C hot water, let it stand for stratification, and separate the lower water layer; then heat up to 75°C, add an appropriate amount of methanol and cool down to 15°C; filter, The filter cake is further washed 1-3 times with an appropriate amount of methanol, and then dried under vacuum to obtain the DBpA intermediate; sodium hydroxide solution, tetrabutylammonium bromide, p-methoxyaniline, benzyl chloride The weight ratio is 170:1.5:70:160;

[0015] (2) Add fuming sulfuric a...

Embodiment 2

[0017] Example 2, a 2'-[(bis(phenylmethyl)amino]-6'-(diethylamino)-spiro(isobenzofuran-1(3H),9'-(9H)xanthene ) The preparation method of-3-ketone, its step is as follows:

[0018] (1) Add sodium hydroxide solution with a mass concentration of 35% to the reaction vessel, phase transfer catalyst tetrabutylammonium bromide, p-methoxyaniline, raise the temperature to 80°C, add benzyl chloride dropwise; then heat the reaction Heat the material to 110°C and keep it warm for 8 hours, then cool down to 90°C, add 90°C hot water, let stand to separate layers, and separate the lower water layer; then heat up to 85°C, add an appropriate amount of methanol and cool down to 25°C; filter, The filter cake is further washed 1-3 times with an appropriate amount of methanol, and then dried under vacuum to obtain the DBpA intermediate; sodium hydroxide solution, tetrabutylammonium bromide, p-methoxyaniline, benzyl chloride The weight ratio is 190: 2.2: 80: 180;

[0019] (2) Add fuming sulfuric ...

Embodiment 3

[0021] Example 3, a 2'-[(bis(phenylmethyl)amino]-6'-(diethylamino)-spiro(isobenzofuran-1(3H),9'-(9H)xanthene ) The preparation method of-3-ketone, its step is as follows:

[0022] (1) Add sodium hydroxide solution with a mass concentration of 32% to the reaction vessel, phase transfer catalyst tetrabutylammonium bromide, p-methoxyaniline, raise the temperature to 75°C, add benzyl chloride dropwise; then heat the reaction Heat the material to 100°C and keep it warm for 5 hours, then cool down to 85°C, add 85°C hot water, let it stand for stratification, and separate the lower water layer; then heat up to 80°C, add an appropriate amount of methanol and cool down to 20°C; filter, The filter cake is further washed 2 times with an appropriate amount of methanol, then dried under vacuum, and the discharge obtains the DBpA intermediate; the weight of sodium hydroxide solution, tetrabutylammonium bromide, p-methoxyaniline, benzyl chloride The ratio is 182:1.8:75:170;

[0023] (2) Ad...

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Abstract

The invention relates to a preparation method of 2'-[bis (phenylmethyl) amino]-6'-(diethylamino)-spiro [isobenzofuran-1 (3H), 9'-[9H] xanthen]-3-one. The preparation method comprises the steps of conducting condensation reaction in fuming sulfuric acid by using 2-(hydroxyl-4-diethylamino-2-hydroxybenzoyl) benzoic acid and N, N-diphenylmethyl-p-anisidine, then adding water and methylbenzene, conducting extraction and layering, removing an acid water layer, adding alkali, conducting cyclization reaction, conducting heating and distillation to remove methylbenzene, finally adding methanol for refining and conducting vacuum drying to obtain GREEN refined products. The preparation method has the advantages that since catalysts are added, the reaction yield of 2-(hydroxyl-4-diethylamino-2-hydroxybenzoyl) benzoic acid is improved to 98 percent; since the fuming sulfuric acid is used to replace concentrated sulfuric acid, the amount of generated sulfonate is reduced; and since alkalinity pH (potential of hydrogen) is controlled to be less than 12, the appearance characteristic and the yield of the products are improved and the product yield is improved to more than 82 percent.

Description

technical field [0001] The present invention relates to a preparation method of a pressure-sensitive dye, in particular to a pressure-sensitive green 2'-[(di(phenylmethyl)amino]-6'-(diethylamino)-spiro(isobenzofuran -1(3H), 9'-(9H) xanthene) -3-one preparation method. Background technique [0002] In the prior art, Tianjin University Journal: Natural Science Edition, 1996, 16 (1): 39-42 discloses "Spiro[isobenzofuran-1(3H), 9'-(9H)-zhanton]-ketone -Synthesis and structural analysis of 3 types of compounds【J】." The synthesis is to synthesize the spiro(isobenzofuran-1(3H), 9'-(9H)-2' Spiro with different substituents such as -N,N-dibenzylamino-6'-diethylamino-xanthene)-ketone-3 [isobenzofuran-1 (3H), 9'-(9H)-xanthene] -Keto-3 compounds. Its defect is: this method uses concentrated sulfuric acid as reaction medium, has sulfonate production, and yield is also low. Contents of the invention [0003] The technical problem to be solved by the present invention is to provide a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10
Inventor 伊恩罗伊霍胜涛朱奎李涛李洪伟孔凡祜
Owner 连云港珂玫琳科技有限公司
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