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Method for synthesizing ranitidine

A technology of ranitidine and mixed acid is applied in the field of synthesizing ranitidine, which can solve the problems of serious environmental pollution and unsafe traditional processes, and achieve the effects of reducing potential safety hazards, facilitating industrial production and mild reaction conditions.

Inactive Publication Date: 2017-06-27
SUZHOU HOMESUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In the traditional synthesis process, it is necessary to use carbon disulfide, dimethyl sulfate and other raw materials with severe odor and high toxicity, and when the two fragments are condensed, methyl mercaptan gas will be produced, which is also a gas with serious odor, so the traditional process It is neither safe nor pollutes the environment seriously

Method used

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  • Method for synthesizing ranitidine
  • Method for synthesizing ranitidine
  • Method for synthesizing ranitidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Synthesis of vinylidene chloride

[0035] Add 100g of 1,1,2-trichloroethane into a four-neck flask equipped with a distillation device, heat the feed liquid to 30-35°C, add 100g of 30% sodium hydroxide solution dropwise with a constant pressure dropping funnel, drop During the addition process, the liquid was continuously condensed and received by the distillation device to obtain 70 g of vinylidene chloride with a yield of 96% and a GC purity of >95%.

[0036] (2) Synthesis of 1,1-dichloro-2-nitroethylene

[0037] Add 80g of concentrated hydrochloric acid and 80g of concentrated nitric acid into the three-necked flask, add 60g of vinylidene chloride dropwise at a temperature of 20-25°C, continue to keep warm for 3 hours after dropping, pour into 100g of ice water after the reaction, add 100g of chloroform for extraction , collect the chloroform layer and wash twice with 5% sodium bicarbonate solution, dry the washed chloroform with anhydrous magnesium sulfate for ...

Embodiment 2

[0045] (1) Synthesis of vinylidene chloride

[0046] Add 100g of 1,1,2-trichloroethane into a four-neck flask equipped with a distillation device, heat the feed liquid to 30°C, and add 110g of 30% sodium hydroxide solution dropwise with a constant pressure dropping funnel. The liquid is continuously condensed and received by the distillation device to obtain vinylidene chloride.

[0047] (2) Synthesis of 1,1-dichloro-2-nitroethylene

[0048] Add 62g of concentrated hydrochloric acid and 68g of concentrated nitric acid into the three-necked flask, control the temperature and add 65g of vinylidene chloride dropwise at 20°C, continue the heat preservation reaction for 2 hours after dropping, pour into 100g of ice water after the reaction, add 100g of dichloromethane for extraction , the dichloromethane layer was collected and washed twice with 5% sodium bicarbonate solution, and the washed dichloromethane was dried with anhydrous magnesium sulfate for 1 hour, filtered, and conce...

Embodiment 3

[0056] (1) Synthesis of vinylidene chloride

[0057] Add 100g of 1,1,2-trichloroethane into a four-necked flask equipped with a distillation device, heat the feed liquid to 35°C, and add 100g of 30% sodium hydroxide solution dropwise with a constant pressure dropping funnel. The liquid is continuously condensed and received by the distillation device to obtain vinylidene chloride.

[0058] (2) Synthesis of 1,1-dichloro-2-nitroethylene

[0059] Add 82g of concentrated hydrochloric acid and 98g of concentrated nitric acid into the three-necked flask, add 60g of vinylidene chloride dropwise at a temperature of 20-25°C, and continue to keep warm for 4 hours. After the reaction, pour into 100g of ice water and extract with 100g of chloroform. , the chloroform layer was collected and washed twice with 5% sodium bicarbonate solution, and the washed chloroform was dried with anhydrous magnesium sulfate for 1 hour, filtered, and concentrated to obtain 1,1-dichloro-2-nitroethylene.

...

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Abstract

A method for synthesizing ranitidine includes following steps: 1), dropwise adding sodium hydroxide water solution into 1, 1, 2-trichloroethane at 30-35 DEG C for reaction to obtain vinylidene chloride, wherein a mass ratio of 1, 1, 2-trichloroethan to sodium hydroxide is 1:0.3-0.33; 2), dropwise adding vinylidene chloride into mixed acid of concentrated hydrochloric acid and concentrated nitric acid at 20-25 DEG C for reaction for 2-4h, wherein a consumption ratio of vinylidene chloride to the mixed acid is 1:2-3; 3), adding cysteamine hydrochloride into sodium hydroxide and potassium hydroxide solution, and dropwise adding a product of the step 2) at 50-55 DEG C to obtain a closed-loop product; 4), enabling the closed-loop product to react with alcohol or methanol solution at room temperature for 14-18h to obtain an open-loop product; 5), adding the open-loop product and 2-[(dimethylamino)methyl]-5 chloromethyl-furan into potassium hydroxide or sodium hydroxide water solution for reaction at 40-50 DEG C for 2-4h to obtain ranitidine. The method lowers potential safety hazards and is simple and easy for industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing ranitidine. Background technique [0002] Ranitidine hydrochloride (Ranitidine hydrochloride), the chemical name is N'-methyl-N-[2[[5-[(dimethylamino)methyl-2-furyl]methyl]thio]ethyl] -2-Nitro-1,1-ethylenediamine hydrochloride is a histamine H2 receptor blocker, which can inhibit basic gastric acid secretion and stimulated gastric acid secretion, and can also inhibit the secretion of pepsin. It was launched by GlaxoSmithKline in 1983 and has good clinical efficacy after listing. Therefore, although it has a history of more than 30 years, it is still selling well both at home and abroad. [0003] Due to the improvement of people's living standards, digestive system diseases are one of the common frequently-occurring diseases, among which peptic ulcer is the main one, mainly caused by smoking, drinking, emotional stress, and drug stimulation. 10-20% of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/52
CPCC07D307/52
Inventor 樊超翟金星陆志丹
Owner SUZHOU HOMESUN PHARMA
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