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Industrialization production method of 2-mercapto-1-methylimidazole

A technology of methylimidazole and its production method, which is applied in the field of industrialized production, can solve the problems of not finding a synthesis scheme of 2-mercapto-1-methylimidazole, and not giving a synthesis scheme of 2-mercapto-1-methylimidazole, etc.

Active Publication Date: 2013-07-24
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In J.Am.Chem.Soc.,71,4000.(1949), it is described that substituted amino acetal reacts with thiocyanic acid to prepare derivatives of 2-mercapto-1-methylimidazole, but it is given in the text It is only applied to a small amount of reaction on a laboratory scale, and the article does n...

Method used

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Embodiment 1

[0019] (a) Pump 480 kg of absolute ethanol and 180 kg of vinyl acetate into the No. 1 reactor. After the pumping is completed, nitrogen balances the vacuum in the reactor. During the reaction process, the temperature of the reaction solution was controlled at about 5°C, and 335 kg of bromine was pressed into the No. 1 reactor, and the addition was completed in about 10 hours. After the addition of bromine, the temperature was raised to 30°C, and the reaction was kept until the reaction liquid was sampled and GC detected that the intermediate was ≤ 1.0%, that is, the reaction was stopped.

[0020] Under stirring, transfer the pre-prepared 16.7% sodium carbonate aqueous solution into the No. 1 reaction kettle until the pH of the reaction solution is 8, then add 540 kg of dichloromethane, stir for 30 minutes, and separate the organic layer.

[0021] Add 300 kilograms of water and 60 kilograms of sodium chloride in No. 2 reactor, after stirring and dissolving completely, then add ...

Embodiment 2

[0027] (a) Pump 480 kg of absolute ethanol and 180 kg of vinyl acetate into the No. 1 reactor. After the pumping is completed, nitrogen balances the vacuum in the reactor. During the reaction process, the temperature of the reaction solution was controlled at about 5°C, and 335 kg of bromine was pressed into the No. 1 reactor, and the addition was completed in about 10 hours. After the addition of bromine, the temperature was raised to 30°C, and the reaction was kept until the reaction liquid was sampled and GC detected that the intermediate was ≤ 1.0%, that is, the reaction was stopped.

[0028] Under stirring, transfer the pre-prepared 16.7% sodium carbonate aqueous solution into the No. 1 reaction kettle until the pH of the reaction solution is 10, then add 540 kg of dichloromethane, stir for 30 minutes, and separate the organic layer.

[0029] Add 300 kilograms of water and 60 kilograms of sodium chloride in No. 2 reactor, after stirring and dissolving completely, then add...

Embodiment 3

[0035] (a) Pump 480 kg of absolute ethanol and 180 kg of vinyl acetate into the No. 1 reactor. After the pumping is completed, nitrogen balances the vacuum in the reactor. During the reaction process, the temperature of the reaction solution was controlled at about 5°C, and 335 kg of bromine was pressed into the No. 1 reactor, and the addition was completed in about 10 hours. After the addition of bromine, the temperature was raised to 30°C, and the reaction was kept until the reaction liquid was sampled and GC detected that the intermediate was ≤ 1.0%, that is, the reaction was stopped.

[0036] Under stirring, transfer the pre-prepared 16.7% sodium carbonate aqueous solution into the No. 1 reaction kettle until the pH of the reaction solution is 9, then add 540 kg of dichloromethane, stir for 30 minutes, and separate the organic layer.

[0037] Add 300 kilograms of water and 60 kilograms of sodium chloride in No. 2 reactor, after stirring and dissolving completely, then add ...

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Abstract

The invention relates to an industrialization production method of antithyroid drug 2-mercapto-1-methylimidazole. The method comprises: (a) reacting vinyl acetate with bromine in absolute ethyl alcohol, regulating a pH value into alkalescence after reaction, obtaining a bromoacetaldehyde diethyl acetal crude product after extraction and desolventization, and directly adding the bromoacetaldehyde diethyl acetal crude product into a next step of reaction; (b) performing aminolysis reaction of bromoacetaldehyde diethyl acetal and methylamine aqueous solution, and after completing reaction, obtaining methylamino acetal through distilling, separating and purifying after extraction and de-watering; (3) dropping hydrochloric acid into aqueous solution of methylamino acetal and potassium rhodanide; removing water in the reaction solution by reduced pressure distillation after reaction, removing a part insoluble in ethyl acetate from the obtained solid, dissolving residual solid into water with pH being 1-2, crystallizing to obtain 2-mercapto-1-methylimidazole with purity higher than 99%, and then vacuum-drying to obtain a finished product. The production method has a short product line, can obtain 2-mercapto-1-methylimidazole with high purity, and has a strong industrialization prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a preparation method of 2-mercapto-1-methylimidazole, in particular to an industrial production method of 2-mercapto-1-methylimidazole. Background technique [0002] 2-Mercapto-1-methylimidazole is an antithyroid drug. Its mechanism of action is to inhibit thyroid peroxidase, thereby hindering the oxidation of iodide absorbed into the thyroid and the coupling of tyrosine, and hindering the synthesis of thyroxine (T4) and triiodothyronine (T3). Animal experiments have observed that it can inhibit the synthesis of antibodies by B lymphocytes, reduce the level of thyroid-stimulating antibodies in the blood circulation, and restore the function of suppressor T cells to normal. It is suitable for various types of hyperthyroidism, including Graves' disease (with autoimmune dysfunction, diffuse thyroid enlargement, exophthalmos), thyroid adenoma, nodular goiter and thyroid cancer. [00...

Claims

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Application Information

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IPC IPC(8): C07D233/84
Inventor 贺宝元邵严亮
Owner XUZHOU B&C CHEM CO LTD
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