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Method for synthesizing ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate

A technology of methylthiopyrimidine and ethyl formate, applied in the field of synthesis of 4-chloro-2-methylthiopyrimidine-5-ethyl carboxylate, which can solve the problems of poor reaction conditions, difficult operation, product decomposition and deterioration, etc. problems, to achieve the effects of cost and productivity improvement, reaction safety improvement, simple and easy operation

Pending Publication Date: 2019-04-30
NANJING HABO MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology involves preparing an Intermediate called 2MES (2-(dimethyloxy)-4'-hydroxy-6' -trimetazolidone), also known by its chemical name: Ethoxynomaleone-3', 5EtNOS 35 or 7ESA3 with specific properties that improve their ability to absorb light at certain wavelength ranges from UV rays into visible lights for use in photography applications. These modifications help make it easier to produce these compounds more efficiently while reducing costs compared to traditional methods like triton X fluorescent dye method.

Problems solved by technology

This patents describes different ways to make certain types of molecules from alkynols like 2-(dimethyloxy)-4'-cyano-3',5 '-dihydro-1H-iminoisoindole (EMI), called Etomycins A through D). These compounds have been found useful because they were discovered earlier than other classes of natural products that had potential applications in medicine and agriculture. However, current techniques involve multiple steps involving starting material with potentially harmful substances like EMEI, dimercaptans, cyclopropenecarbincs, thionitrosemodifications, nitrogen bases, carbohydrates, ammonia, lysophytanes, steroids, alkaloids and others.

Method used

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  • Method for synthesizing ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate
  • Method for synthesizing ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate
  • Method for synthesizing ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate

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Embodiment 1

[0023] first step

[0024]

[0025] Into a clean 20L reaction bottle, add 5kg of water and 5kg of ethanol, and stir evenly. Take 1.8kg of solid sodium hydroxide, add it into the system and stir for 30min. until it is completely dissolved. Cool down to below 25°C in an ice bath, add 3.2 kg of S-methylisothiouronium sulfate, basically no heat release, and a white turbid liquid. After addition, stir for 10 min. Add dropwise the ethanol solution of ethoxymethylene (3.88kg ethoxymethylene + 1.5kg ethanol), exothermic at the initial stage of dropping, keep the temperature below 30°C, basically no heat release later, and the dropping speed can be accelerated. After dropping, the temperature was raised to 65-70°C for 1.5h. The reaction solution was slowly poured into 10 kg of ice water while it was hot, and stirred for 20 min. Centrifuge the treatment liquid in a centrifuge to obtain 4.6kg of wet product. Air-dried at 70-75°C until constant weight. 3.6 kg of off-white solid w...

Embodiment 2

[0027] Add 150kg of water and 150kg of ethanol to a clean 500L reactor, and stir evenly. Take 54kg of solid sodium hydroxide, add it into the system and stir for 60min. until it is completely dissolved. The temperature was lowered to below 25 degrees in an ice bath, and 96 kg of S-methylisothiouronium sulfate was added, basically no heat release, and it was a white turbid liquid. After addition, stir for 30min. Add dropwise the ethanol solution of ethoxymethylene (116.5kg ethoxymethylene + 45kg ethanol), the initial stage of dropwise exothermic, heat preservation below 30 ℃, basically no exothermic later, can speed up the rate of addition. After dropping, the temperature was raised to 65-70°C for 2 hours. The reaction solution was slowly poured into 300 kg of ice water while it was hot, and stirred for 90 min. Centrifuge the treatment liquid in a centrifuge to obtain 135kg of wet product. Air-dried at 70-75°C until constant weight. 105 kg of off-white solid was obtained, ...

Embodiment 3

[0029] second step

[0030]

[0031] Into a clean 20L reaction bottle, add 3.3kg of the intermediate of the first step, 8kg of toluene, and 241g of DMF, and it becomes a cloudy liquid. Add 1200g of thionyl chloride dropwise at room temperature, 1 / 2 of the dropwise exotherm is exothermic, and there is basically no exotherm afterwards, so the dripping can be accelerated. After dropping, stir at 30°C for 30min. Take 1550 g of phosphorus oxychloride and add it dropwise to the reaction solution. Turn on the heating, slowly heat to about 60°C, a large amount of gas is generated, keep warm at 55-60°C and stir for 30min. When heated to about 65°C, the reaction solution gradually changed from turbidity to yellow clear solution. After reacting for 1 h, TLC detected that the reaction of the raw materials was complete. The reaction liquid is lowered to room temperature, slowly poured into 5kg of ice water in batches, it will release heat, preferably not higher than 20°C. Extract w...

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Abstract

The invention belongs to the technical field of organic synthesis, and especially relates to a method for synthesizing ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate. The method comprises the following steps: an intermediate is prepared through cyclization of diethyl ethoxymethylenemalonate and S-methylisothiourea sulfate with sodium oxide as an alkali and ethanol-water as a reaction solvent;and the ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate is synthesized from the intermediate with toluene as a solvent and thionyl chloride and phosphorous oxychloride as a chlorinating reagent.A mixed solution of ethanol and water is used as the reaction solvent to ensure the solubility of the raw materials and make the sodium hydroxide completely dissolved, so the proceeding of the cyclization reaction is benefited, and dangerous substances such as butyl lithium are avoided, thereby the cost of the reaction raw materials is reduced, and the productivity is greatly increased; toluene used as the reaction solvent greatly reduces the use amount of the chlorinating reagent, so the reaction safety is greatly improved, the cost is reduced, and the post-treatment operation is simplified;and the thionyl chloride and phosphorus oxychloride are used as the mixed chlorinating reagent, so the yield of the reaction is greatly increased.

Description

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Claims

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Application Information

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Owner NANJING HABO MEDICAL TECH
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