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A kind of preparation method of 10-methoxy-4h-benzo[4,5] cycloheptatriene[1,2-b]thiazole-4-one

A technology of cycloheptatriene and methoxy, applied in the field of preparation of 10-methoxy-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazole-4-one, It can solve the problems of toxic environment and pollution of the human body, and achieve the effect of less three wastes, convenient post-processing, and no corrosion of equipment

Active Publication Date: 2017-07-25
湖州优研知识产权服务有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Among them, the method currently used for methoxylation is mostly using dimethylformamide (DMF) as a solvent, cuprous chloride or liquid acid-base as a catalyst, so that the raw material reacts with sodium methylate to produce methoxylation, but dimethylformamide Formamide (DMF) and cuprous chloride are toxic to the human body and pollute the environment

Method used

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  • A kind of preparation method of 10-methoxy-4h-benzo[4,5] cycloheptatriene[1,2-b]thiazole-4-one
  • A kind of preparation method of 10-methoxy-4h-benzo[4,5] cycloheptatriene[1,2-b]thiazole-4-one

Examples

Experimental program
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Effect test

Embodiment 1

[0028] (1) Preparation of catalyst

[0029] 1) Put 15.0g of MgO solid into an oven, bake at 100°C for 12h, and set aside;

[0030] 2) Weigh 2.4g of KOH, dissolve it in 50mL of deionized water to make an aqueous potassium hydroxide solution, weigh 10.0g of MgO in step 1), dip into the aqueous potassium hydroxide solution, and ultrasonicate at 40Hz for 30min at room temperature. Immerse at (25°C) for 24 hours, stir and steam at 80°C until viscous;

[0031] 3) Dry the product of step 2) in an oven at 100°C for 24 hours in an air atmosphere, and finally bake it in a muffle furnace at 400°C for 3 hours;

[0032] 4) Grind the product of step 3) to 80-120 meshes to obtain K with a mass loading of 20%. 2 O / MgO solid base catalyst.

[0033] (2) Methoxylation reaction

[0034] Weigh 29.2g (0.1mol) of 9,10-dihydro-9,10-dibromo-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one and 500ml of Mix water and methanol, stir and reflux for 4h, add 1.1g of K prepared in step (1) 2 O / MgO cat...

Embodiment 2

[0036] (1) Preparation of catalyst

[0037] 1) Add 15.0g of Al 2 o 3 Put the solid in an oven, bake at 100°C for 12 hours, and set aside;

[0038]2) Weigh 3.0g of KOH, dissolve in 50mL of deionized water to make potassium hydroxide aqueous solution, weigh 10.0g of Al in step 1) 2 o 3 , impregnated into aqueous potassium hydroxide solution, ultrasonicated at 40 Hz for 30 minutes at room temperature, immersed for 12 hours at room temperature, stirred and steamed at 80°C until viscous;

[0039] 3) Dry the product of step 2) in an oven at 100°C for 12 hours in an air atmosphere, and finally bake it in a muffle furnace at 350°C for 4 hours;

[0040] 4) Grind the product of step 3) to 80-120 meshes to obtain K with a mass loading of 25%. 2 O / Al 2 o 3 solid base catalyst.

[0041] (2) Methoxylation reaction

[0042] Weigh 29.2g (0.1mol) of 9,10-dihydro-9,10-dibromo-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one and 500ml of Mix water and methanol, stir and reflux for 4h,...

Embodiment 3

[0044] (1) Preparation of catalyst

[0045] 1) Add 15.0g of CaCO 3 The solid was calcined at 900°C for 5 hours, cooled and dried to obtain a CaO solid for use;

[0046] 2) Weigh Na 2 CO 3 1.71g, dissolved in 100mL deionized water, weighed 10.0g of CaO in step 1), impregnated into Na 2 CO 3 In the aqueous solution, ultrasonic at 40Hz for 30min at room temperature, soak at room temperature for 24h, stir and steam at 80°C until viscous;

[0047] 3) Dry the product of step 2) in an oven at 90°C for 24 hours in an air atmosphere, and finally bake it in a muffle furnace at 450°C for 3.5 hours;

[0048] 4) Grinding the product of step 3) to 80-120 meshes to obtain Na with a mass loading capacity of 10%. 2 O / CaO solid base catalyst.

[0049] (2) Methoxylation reaction

[0050] Weigh 29.2g (0.1mol) of 9,10-dihydro-9,10-dibromo-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one and 500ml of Mix water and methanol, stir and reflux for 3h, add 2.92g Na 2 O / CaO catalyst (the mass ...

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Abstract

The present invention discloses a 10-methoxy-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one preparation method, which comprises: mixing a raw material 9,10-dihydro-9,10-dibromo-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one and absolute methanol, carrying out stirring reflux for 2-6 h, adding a solid alkali catalyst to the reaction solution, continuously carrying out the reflux reaction for 2-6 h, carrying out separation purification on the reaction solution after completing the reaction, and recovering the solid alkali catalyst so as to obtain the product 10-methoxy-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one. According to the present invention, the solid alkali catalysis is used, the technology is easy to operate, the equipment is not corroded, the three-waste is less, the post-treatment is easy, the solid alkali can be reused, and the preparation method is the economical and practical green environmental protection technology.

Description

[0001] (1) Technical field [0002] The present invention relates to a method for preparing 10-methoxy-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one, in particular to a method using solid base to catalyze 9, Method for the methoxylation of 10-dihydro-9,10-dibromo-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one. [0003] (2) Background technology [0004] 10-Methoxy-4H-benzo[4,5]cycloheptatriene[1,2-b]thiazol-4-one is a key intermediate in the synthesis of ketotifen maleate. Ketotifen maleate is a potent oral allergy mediator release agent, it can inhibit mast cells from releasing histamine and allergic slow-response substances, and has a strong H1 receptor antagonistic effect. In addition, it antagonizes serotonin and the slow-reacting substances of allergies. It can also directly antagonize the contraction of histamine and slow-reacting substances on bronchial smooth muscle. It is clinically used for the prevention and treatment of exogenous, endogenous and mixed asth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/80B01J23/04B01J23/06
CPCB01J23/04B01J23/06C07D333/80
Inventor 裴文杨涛孙莉王海滨杨振平
Owner 湖州优研知识产权服务有限公司
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