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Medicine intermediate 2-phenoxy aniline and preparation method thereof

A technology of phenoxyaniline and phenoxymethanesulfonanilide is applied in the field of pharmaceutical intermediate 2-phenoxyaniline and its preparation, and can solve the problems of low product purity, incomplete reaction, low yield and the like, and achieves Overcome separation difficulties, improve product yield, and overcome the effects of low purity

Inactive Publication Date: 2011-05-25
荆州市丽之源化工科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The reaction of condensation of halogenated nitrobenzene and phenol to form phenyl ether has always been a difficult point in organic synthesis. The traditional synthesis of 2-phenoxyaniline mostly uses the method of direct condensation of o-nitrochlorobenzene and phenol at high temperature, which not only consumes a lot of energy High, incomplete reaction, many side reactions, difficult to purify, resulting in low product purity, low yield, high cost, difficult to treat phenolic wastewater, heavy pollution, not suitable for industrial production, long-term dependence on imports

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Preparation of catalyst

[0024] Take 10 parts by weight of solid L-tertiary amine alkaloid, carry out steam distillation at a temperature of 100-120°C, collect 8 parts by weight of condensate, and add 1 Solid NaOH twice the weight of the condensate, control the pH value of the mixed solution in the range of 13, and place it naturally for 48-60 hours at normal temperature and pressure to prepare the catalyst;

[0025] (2) 100 parts by weight of o-nitrochlorobenzene, 65 parts by weight of phenol, and 7 parts by weight of the catalyst prepared in step (1) are added to the reactor under stirring Middle, heat preservation in sections, the first heat preservation temperature is 80-85°C, heat preservation for 5 hours, the second heat preservation temperature is 145-155°C, heat preservation for 8 hours, central control sampling, the intermediate product 2-phenoxy Nitrobenzene;

[0026] (3) Separation and purification

[0027] Add 150 parts by weight of water to the prod...

Embodiment 2

[0032] (1) Preparation of catalyst

[0033] Take 15 parts by weight of solid D-tertiary amine alkaloid, carry out steam distillation at a temperature of 100-120°C, collect 13 parts by weight of condensate, and add 2 times the weight of solid NaOH of the condensate, control the pH value of the mixed solution in the range of 13.5, and place it naturally for 48-60 hours at normal temperature and pressure to prepare the catalyst;

[0034] (2) 110 parts by weight of o-nitrochlorobenzene, 74 parts by weight of phenol, and 10 parts by weight of the catalyst prepared in step (1) were added to the reactor under stirring Middle, heat preservation in sections, the first heat preservation temperature is 80-85°C, heat preservation for 5 hours, the second heat preservation temperature is 145-155°C, heat preservation for 8 hours, central control sampling, the intermediate product 2-phenoxy Nitrobenzene;

[0035] (3) Separation and purification

[0036] Add 150 parts by weight of water to ...

Embodiment 3

[0041] (1) Preparation of catalyst

[0042] Take 18 parts by weight of solid L-tertiary amine alkaloid, carry out steam distillation at a temperature of 100-120°C, collect 17 parts by weight of condensate, add 4 Solid NaOH twice the weight of the condensate, control the pH value of the mixed solution in the range of 14, and place it naturally for 48-60 hours at normal temperature and pressure to prepare the catalyst;

[0043] (2) 120 parts by weight of o-nitrochlorobenzene, 80 parts by weight of phenol, and 12 parts by weight of the catalyst prepared in step (1) are added to the reactor under stirring Middle, heat preservation in sections, the first heat preservation temperature is 80-85°C, heat preservation for 5 hours, the second heat preservation temperature is 145-155°C, heat preservation for 8 hours, central control sampling, the intermediate product 2-phenoxy Nitrobenzene;

[0044] (3) Separation and purification

[0045] Add 150 parts by weight of water to the product ...

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PUM

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Abstract

The invention provides a medicine intermediate 2-phenoxy aniline and a preparation method thereof. The molecular formula of the medicine intermediate 2-phenoxy aniline is C12H11ON and the medicine intermediate 2-phenoxy aniline comprises the following components in parts by weight: 100-120 parts of o-nitrochlorobenzene, 65-80 parts of phenol, 7-12 parts of catalyst, 5-12 parts of active nickel and 400-700 parts of ethanol. A preparation method of the catalyst is characterized by taking 10-18 parts by weight of solid laevorotatory or dextrorotatory tertiary amine alkaloids, carrying out steam distillation at the temperature of 100-120 DEG C, collecting the condensate, adding solid NaOH with weight being 1-4 times of that of the condensate to the collected condensate, controlling the pH value of the mixed solution between 13 and 14 and naturally standing for 48-60 hours, thus preparing the catalyst. The preparation method of 2-phenoxy aniline comprises the following steps: (1) preparing the catalyst; (2) preparing an intermediate product 2-phenoxy nitrobenzene; (3) carrying out separation and purification; (4) recovering the catalyst; and (5) preparing the medicine intermediate 2-phenoxy aniline.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a medicine intermediate 2-phenoxyaniline and a preparation method thereof. Background technique [0002] 2-Phenoxyaniline is an essential intermediate raw material for the specific analgesic drug Nimesulide (4-nitro-2-phenoxymethanesulfonanilide). The drug was first launched in Italy in 1985, and is now widely used in 17 countries around the world. A large number of clinical verification documents in various countries indicate that nimesulide has a wide range of anti-inflammatory and analgesic effects, not only can quickly relieve toothache, menstrual pain, post-operative Pain and other pain, and can effectively improve pelvic inflammatory disease, otitis, laryngitis and other related symptoms, high bioavailability, good gastrointestinal tract, liver and kidney tolerance, is a new generation of highly selective, strong Effective, safe anti-inflammatory pain reliever...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/90C07C213/02
CPCY02P20/584
Inventor 姚彦章卢胜兰孙朝晖
Owner 荆州市丽之源化工科技股份有限公司