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Production method of cimetidine

A production method and technology of cimetidine, which are applied in the field of preparation of cimetidine, can solve problems such as harm to human body and environment, high production cost, environmental pollution, etc., and achieve mild reaction conditions, little environmental pollution and low price. Effect

Active Publication Date: 2021-08-10
SHIJIAZHUANG POLEE PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw material cyanogen chloride has tear gas, which is harmful to the human body and the environment, and it is not easy to obtain commercially.
Other reported synthetic routes also have disadvantages such as difficult availability of raw materials, high production costs, environmental pollution, and unsuitability for industrial production.

Method used

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  • Production method of cimetidine
  • Production method of cimetidine
  • Production method of cimetidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Dissolve 83.6Kg (1.1Kmol) NH4SCN in 500L water, add 1.45Kg (0.01Kmol) ammonium iodide, then add 80.5Kg (1Kmol) 2-chloroethanol, reflux for 3 hours, cool down to room temperature, stand still, and remove water layer, the oil layer was washed with water, dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain intermediate (I). Yield 82.3%. Elemental analysis: C3H5NOS, calculated: C, 34.93, H, 4.89, N, 13.58, S, 31.09; found: C, 34.90, H, 4.91, N, 13.61, S, 31.07. 1H NMR (400MHz, CDCl3) δ2.85 (br, s, 1H), 3.60 (m, 2H), 3.79 (m, 2H).

[0028] Dissolve 103Kg (1Kmol) of intermediate (I) in 350L of ethanol, add 116.3Kg of monomethylamine solution with a mass fraction of 40%, react at 50°C for 3h, evaporate to dryness under reduced pressure to obtain intermediate (II), and use the crude product directly react in the next step. Elemental Analysis: C4H10N2OS, Calculated: C, 35.80, H, 7.51, N, 20.87, S, 23.89; Found: C, 35.83, H, 7.52, N, 2...

Embodiment 2

[0033] Dissolve 85.1Kg (1.05Kmol) NaSCN in 500L water, add 4.5Kg (0.03Kmol) sodium iodide, then add 80.5Kg (1Kmol) 2-chloroethanol, reflux for 5h, cool down to room temperature, stand still, and remove water layer, the oil layer was washed with water, dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain intermediate (I). Yield 84.5%.

[0034]Dissolve 103Kg (1Kmol) of intermediate (I) in 350L of ethanol, add 155Kg of monomethylamine solution with a mass fraction of 40%, react at 60°C for 3h, and evaporate to dryness under reduced pressure to obtain intermediate (II). The crude product was directly used in the next reaction.

[0035] Add 134Kg (1Kmol) of intermediate (II) into 300L of acetic acid, stir, cool down to 8-10°C, add dropwise 1013Kg of peracetic acid solution with a mass fraction of 30%, control the rate of addition, make the temperature of the reaction system 20°C, add dropwise After completion, react at room temperature for...

Embodiment 3

[0039] Dissolve 116.4Kg (1.2Kmol) KSCN in 500L water, add 0.97Kg (0.02Kmol) potassium iodide, then add 80.5Kg (1Kmol) 2-chloroethanol, reflux for 3 hours, lower to room temperature, let stand, and separate the water layer, The oil layer was washed with water, dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain intermediate (I). Yield 85.3%.

[0040] Dissolve 103Kg (1Kmol) of intermediate (I) in 400L of ethanol, add 116.2Kg of monomethylamine solution with a mass fraction of 40%, react at 55°C for 2h, and evaporate to dryness under reduced pressure to obtain intermediate (II). The crude product was directly used in the next reaction.

[0041] Add 134Kg (1Kmol) of intermediate (II) into 350L of acetic acid, stir, cool down to 8-10°C, add dropwise 760Kg of peracetic acid solution with a mass fraction of 35%, control the rate of addition, make the temperature of the reaction system 15°C, add dropwise After completion, react at room tempe...

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Abstract

The invention relates to a production method of cimetidine, the production method comprises the following steps: (1) reacting 2-chloroethanol with thiocyanate to prepare an intermediate (I); (2) reacting the intermediate (I) with methylamine to prepare an intermediate (II); (3) oxidizing the intermediate (II) with oxyacetic acid to obtain an intermediate (III); (4) condensing the intermediate (III) and cyanamide to obtain an intermediate (IV); and (5) condensing the intermediate (IV) and imidazole mercaptan (V) to prepare cimetidine. The production method of cimetidine is provided, the production method can avoid the environmental pollution caused by the by-product methyl mercaptan generated in the existing cimetidine production, and is simple in production process, low in production cost and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to an environment-friendly and low-cost preparation method of cimetidine. Background technique [0002] Cimetidine is a selective H2 receptor antagonist that mainly inhibits gastric acid secretion and is used for the treatment of peptic ulcer. Since the advent of cimetidine, many technological routes have been reported at home and abroad, the purpose of which is to shorten the reaction steps, improve process conditions, eliminate environmental pollution, and reduce production costs. At present, large-scale production of cimetidine at home and abroad mostly adopts the following process route: [0003] [0004] The disadvantage of this route is that the total yield is low, about 46%, and produces methyl mercaptan as a by-product, which has a foul smell and pollutes the environment. Japanese patent JP82-56465 reports the method of condensing phenol, cyanogen chloride and cyana...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64
CPCC07D233/64
Inventor 秦晓辉史兰香张之奎秦建辉刘胜昔杨旭翠秦正浩秦少博
Owner SHIJIAZHUANG POLEE PHARMA CO LTD
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