Method for preparing substituted spirooxazine photochromic compound

A photochromic and compound technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of low yield of photochromic compounds, expensive preparation cost, etc., and achieve bright color and low preparation cost. , the effect of high yield

Inactive Publication Date: 2012-05-30
TIANJIN FORESEEN TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is to provide a preparation method for substituted spirooxazine photochromic compounds, adopt an intermediate process for forming copper complexes, and overcome the difficulties of preparing substituted spirooxazine photochromic compounds using the prior art The disadvantages of low yield and relatively expensive preparation cost

Method used

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  • Method for preparing substituted spirooxazine photochromic compound
  • Method for preparing substituted spirooxazine photochromic compound
  • Method for preparing substituted spirooxazine photochromic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of photochromic compound 1,3,3-trimethyl-6'-tetrahydropyrrole-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4]oxa Zinc.

[0029] The first step, the preparation of 1-nitroso-2-naphthol copper complex

[0030] 1.36 g of CuCl 2 It is configured as the aqueous solution A that the mass percentage concentration is 30%, and 3.95 grams of 1-nitroso-2-naphthols are dissolved in the mixed solvent that the volume ratio is 1: 1 tetrahydrofuran and water, and configuration is that concentration is 0.04g / mL of solution B, as CuCl 2 The mass ratio of 1-nitroso-2-naphthol is 1:2.9, the solution A is added dropwise to the solution B under stirring, and the stirring is continued for 15 minutes, then suction filtered and dried to obtain the product 1- Nitroso-2-naphthol copper complex 3.91 g, yield 96%.

[0031] The second step, 1,3,3-trimethyl-6'-tetrahydropyrrole-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine Synthesis

[0032] In a 100mL three-necked round-bottomed fla...

Embodiment 2

[0034] Preparation of photochromic compound 1,3,3-trimethyl-6'-morpholine-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine .

[0035] The first step, the preparation of 1-nitroso-2-naphthol copper complex

[0036] With embodiment 1.

[0037] The second step, 1,3,3-trimethyl-6'-morpholine-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine synthesis

[0038] In a 100mL three-necked round-bottomed flask, add 1mmol of the 1-nitroso-2-naphthol copper complex and 4mmol of morpholine prepared in the first step, and dissolve them in the 20mL of the three-necked round-bottomed flask first In ethanol, heat to reflux for 3 hours, then add 15 mL of 1,3,3-trimethyl-2-methyleneindoline ethanol solution with a concentration of 0.1 mmol / mL, continue to heat and reflux for 9 hours, monitor by TLC, stop the reaction Afterwards, use column chromatography to separate the photochromic compound 1,3,3-trimethyl-6'-morpholine-spiroindoline-2,3'[3H]naphtho[2,1-b The solid product of ][1,4]oxazine...

Embodiment 3

[0040] Preparation of photochromic compound 5-chloro-1,3,3-trimethyl-6'-tetrahydropyrrole-spiroindoline-2,3'-[3H]naphtho[2,1-b][1 , 4] Oxazine.

[0041] The first step, the preparation of 1-nitroso-2-naphthol copper complex

[0042] With embodiment 1.

[0043] In the second step, 5-chloro-1,3,3-trimethyl-6'-tetrahydropyrrole-spiroindoline-2,3'-[3H]naphtho[2,1-b][1, 4] Synthesis of oxazines

[0044] In a 100mL three-necked round-bottomed flask, add 1mmol of the 1-nitroso-2-naphthol copper complex prepared in the first step and 3.5mmol tetrahydropyrrole, and dissolve them in the three-necked round-bottomed flask first 20mL of ethanol, heated to reflux for 3 hours, then added 15mL of ethanol solution of 5-chloro-1,3,3-trimethyl-2-methyleneindoline with a concentration of 0.1mmol / mL, and continued to heat and reflux for 5 hours, TLC monitoring, after stopping the reaction, separated by recrystallization to obtain the photochromic compound 5 chloro-1,3,3-trimethyl-6'-tetrahydro...

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Abstract

The invention relates to a method for preparing a substituted spirooxazine photochromic compound, relating to an organic photochromic material. The method comprises the steps of synthesizing 1-nitroso-2-naphthol metal complex and synthesizing the substituted spirooxazine photochromic compound. In the formula, R1 represents C1, H or CH3; R2 represents CH3; and R3 is shown in the specification. According to the method disclosed by the invention, an intermediate process for forming a copper complex is adopted, therefore, the preparation yield is up to 20-76%; furthermore, the process is simple; the preparation cost is low; and the prepared substituted spirooxazine photochromic compound has the characteristics of good endurance, bright colour, high yield and wide application range.

Description

technical field [0001] The technical scheme of the invention relates to an organic photochromic material, specifically a preparation method of a substituted spirooxazine photochromic compound. Background technique [0002] Substituted spirooxazine photochromic compounds are a class of organic photochromic materials used in the fields of optical information materials and anti-counterfeiting identification materials. The same main inventor of the present invention has developed 6'-heterocyclic substituted spirooxazine photochromic compounds and their preparation methods (see CN1629249). However, the production rate of substituted spirooxazine photochromic compounds prepared by this prior art is not high, and the preparation cost is relatively expensive; the same main inventor of the present invention has recently disclosed the synthesis of A method for substituting spirooxazine photochromic compounds (see "Synthesis, 2010, 15, 3418-3422"). This method improves the yield of p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10C09K9/02
Inventor 孟继本庞美丽韩杰
Owner TIANJIN FORESEEN TECH
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