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Method for preparing methocarbamol

A technology of methocarbamol and carbonate, which is applied in the field of chemical synthesis, can solve the problems of low economic efficiency and large amount of dimethyl carbonate, and achieve the effects of good economic benefits, less pollution, and less dosage

Inactive Publication Date: 2019-07-05
ZHEJIANG HAIZHOU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] The safety of this process is relatively good. The green reagent DMC is used, and the process operation is simple. The disadvantage is that the amount of dimethyl carbonate is relatively large, generally 2-5 molar equivalents, the yield is only about 70%, and the economic efficiency is low.

Method used

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  • Method for preparing methocarbamol
  • Method for preparing methocarbamol
  • Method for preparing methocarbamol

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Experimental program
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Embodiment 1

[0036] Embodiment 1: the preparation of methocarbamol

[0037] Add guaiacol glycerin ether 40g (0.2mol), lithium hydroxide 0.2g (0.0083mol), DMAP 0.1g (0.00082mol) in 500ml reaction bottle, warm up to 80 ℃ and add dropwise dimethyl carbonate 22g (0.24mol ), the dropwise addition was completed and refluxed for 4 hours, and TLC followed the reaction process. After the reaction, cool to 40°C, add 34g (0.4mol) of 20% ammonia solution, and react at this temperature for 6 hours to obtain crude methocarbamol, which is recrystallized with 100ml of pure water to obtain 45.6g, yield 95% .

Embodiment 2

[0038] Embodiment 2: the preparation of methocarbamol

[0039] Add guaiacol glycerin ether 40g (0.2mol), sodium hydroxide 0.32g (0.008mol), DMAP 0.1g (0.00082mol) in 500ml reaction bottle, warm up to 80 ℃ and add dropwise dimethyl carbonate 22g (0.24mol ), the dropwise addition was completed and refluxed for 4 hours, and TLC followed the reaction process. After the reaction, cool to 40°C, add 34g (0.4mol) of 20% ammonia solution, and react at this temperature for 6 hours to obtain crude methocarbamol, which is recrystallized with 100ml of pure water to obtain 44.6g, with a yield of 93%. .

Embodiment 3

[0040] Embodiment 3: the preparation of methocarbamol

[0041] Add guaiacol glycerin ether 40g (0.2mol), potassium hydroxide 0.45g (0.008mol), DMAP 0.1g (0.00082mol) in 500ml reaction bottle, warm up to 80 ℃ and add dropwise dimethyl carbonate 22g (0.24mol ), the dropwise addition was completed and refluxed for 4 hours, and TLC followed the reaction process. After the reaction, cool to 40°C, add 34g (0.4mol) of 20% ammonia solution, and react at this temperature for 6 hours to obtain crude methocarbamol, which is recrystallized with 100ml of pure water to obtain 43.2g, yield 90% .

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Abstract

The invention discloses a method for preparing methocarbamol. The method comprises the steps that guaifenesin serves as a raw material, alkali and 4-dimethylaminopyridine serve as a catalyst, carbonicester serves as an esterification agent, and a compound shown in the formula (I) is obtained through an esterification reaction, the compound shown in the formula (I) reacts with ammonia water through an ammoniation reaction to obtain the methocarbamol shown in the formula (II), and the reaction equation of the methocarbamol is that the alkali is hydroxide or carbonate of the first main alkali metal group. Accordingly, guaifenesin serves as a raw material, the alkali and DMAP serves as the catalyst, the carbonic ester is catalyzed to be esterified and then ammonified and crystallized, and themethocarbamol is obtained. A nucleophilic reagent DMAP is used for catalysis, the carbonic ester can rapidly and highly selectively complete the reaction with hydroxide radical, and the high-yield guaifenesin ester is obtained; in addition, the dosage of the carbonic ester is small, safety and environmental protection are achieved, pollution is small, the economic benefit is high, operation is easy, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing a compound, in particular to a method for preparing methocarbamol, and belongs to the technical field of chemical synthesis. Background technique [0002] Methocarbamol is a white crystalline powder. MP: 92-94°C, soluble in ethanol, propylene glycol, toluene and other organic solvents. [0003] Common name: Shujinling [0004] Chemical name: (±)-3-(O-methoxyphenoxy)1,2-propanediol-1-carboxamide. [0005] English name: Methocarbamol [0006] Structural formula: [0007] [0008] Methocarbamol is a central muscle relaxant, which has a selective effect on the central nervous system, especially on neurons in the spinal cord, and obviously inhibits the synaptic reflex related to skeletal muscle spasm, which is caused by anti-strychnine and electrical stimulation Convulsive effect, and has analgesic, analgesic, anti-inflammatory effects. It was originally an antispasmodic drug synthesized by Robers Mur...

Claims

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Application Information

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IPC IPC(8): C07C269/04C07C271/12C07D317/36
CPCC07C269/04C07D317/36C07C271/12
Inventor 王俊华怀哲明虞选旺段香江陈曦
Owner ZHEJIANG HAIZHOU PHARMA CO LTD
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