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Preparation method of 1-mesyl-2-imidazolidone

A technology of imidazolidinone and methylsulfonyl, which is applied in the field of preparation of 1-methanesulfonyl-2-imidazolidinone, which can solve the problems of high requirements for reaction solvents, easy decomposition, difficult control of synthesis process, etc., and achieve safe operation No hidden dangers, few wastes, and wide-ranging sources

Inactive Publication Date: 2010-11-24
上海东满进出口有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1-methanesulfonyl-2-imidazolidinone is an intermediate for the preparation of drugs satrinidazole and mezlocillin, and the current synthesis method of 1-methylsulfonyl-2-imidazolidinone is under the action of alkali such as NaH, with 2 -Imidazolidinone and methanesulfonyl chloride are synthesized as raw materials. However, methanesulfonyl chloride is a liquid highly toxic chemical that is easily decomposed when exposed to water. The requirements for transportation conditions and equipment, as well as the requirements for the reaction solvent are relatively high, which does not meet environmental protection requirements. Requirements and potential safety hazards in operation, and literature reports, the reaction yield of methanesulfonyl chloride and imidazolidinone is unstable, and the synthesis process is difficult to control

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In a 100mL three-necked flask, add 20mL of methanesulfonic acid, heat the oil bath to 95°C, and slowly drop the For thionyl chloride, the temperature of the reaction system was kept at about 80°C after the dropwise addition was started. After the dropwise addition was completed, the constant pressure dropping funnel was removed, and the temperature of the reaction system gradually rose, and the temperature of the reaction system was kept at 90-95°C for 3.5 hours.

[0018] After the reaction, the system was cooled to room temperature, changed to reflux in a vacuum distillation device, and the fraction at 120-126°C was collected at 10mmHg. The fraction turned into a white solid in the air condenser, and 24.757g of the white solid was scraped off to obtain 24.757g of the white solid, melting point 69-70°C, yield 92.4%.

Embodiment 2

[0020] In a 50mL three-neck flask, add 10mL of methanesulfonic acid, heat the oil bath to 95°C, and slowly drop chlorine into the bottle with a constant pressure dropping funnel at a ratio of methanesulfonic acid to thionyl chloride molar ratio of 1:1.5. After the addition of sulfoxide, the temperature of the reaction system was kept at about 80°C. After the dropwise addition was completed, the constant pressure dropping funnel was removed, and the temperature of the reaction system rose gradually. Keep the temperature of the reaction system between 90-95°C for 4.5 hours.

[0021] After the reaction, the reaction system was cooled to room temperature, and an appropriate amount of anhydrous ether was added for recrystallization to obtain 12.224 g of a white solid, melting point: 68-70° C., yield 91.2%.

[0022] 2. Synthesis of 1-methylsulfonyl-2-imidazolidinone:

[0023] The purity of 2-imidazolidinone and methanesulfonic anhydride adopted in the following examples is 99%,

Embodiment 3

[0025] Add 6.94g (75mmol) of 2-imidazolidinone into a 250mL three-necked flask, add 100mL of toluene as a solvent, add 6mL (74mmol) of 99% pyridine, heat up to the reflux of the reaction system under stirring conditions, keep the reflux temperature at 65°C for 30min, and then Add 13.60g (78mmol) of methanesulfonic anhydride, the reaction system changes from colorless and clear to orange, and reddish-brown solids appear in the lower layer, and the reaction is refluxed for 5 hours, the reaction is stopped, the organic solvent is removed by rotary evaporation, and recrystallization is carried out with ethanol to obtain the 10.324 g of white solid, yield 83.8%, melting point 188-190°C.

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Abstract

The invention belongs to the technical field of organic synthesis and relates to a preparation method of 1-mesyl-2-imidazolidone. The preparation method of the 1-mesyl-2-imidazolidone is characterized by comprising the following steps of firstly, in a reaction vessel for synthesizing methanesulfonic anhydride, adding methanesulfonic acid, slowly dropping thionyl chloride, enabling the molar ratio of the methanesulfonic acid and the thionyl chloride to be 1:(1-1.5), and carrying out reaction for 3.5-4.5h under the temperature of 90-95 DEG C; and secondly, in a reaction vessel for synthesizing the 1-mesyl-2-imidazolidone, adding 2-imidazolidone, organic solvent and alkali, stirring, rising the temperature to 60-110 DEG C, refluxing for 30-40min, adding the methanesulfonic anhydride, enabling the molar ratio of the 2-imidazolidone, the methanesulfonic anhydride and the alkali to be 1:(1-1.2):(1-1.2), and obtaining a solid product through recrystallization. The invention has the advantages that firstly, used raw materials do not contain a highly toxic product of methylsulfonyl chloride, are safe to operate without a hidden danger and accord with the environmental protection requirements; and secondly, the yield is higher, wherein the yield for synthesizing the methanesulfonic anhydride achieves 90 percent, and the yield for synthesizing the 1-mesyl-2-imidazolidone is above 80 percent.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the preparation of satrnidazole and mezlocillin intermediates, in particular to a preparation method of 1-methanesulfonyl-2-imidazolidinone. Background technique [0002] Satrinidazole is a better antihelminth drug, mainly used for the treatment of schistosomiasis, and has a remarkable effect in killing schistosomiasis, and the main suppliers are all from the United States; mezlocillin sodium is a better antibacterial drug, which belongs to The third-generation penicillin has a strong antibacterial ability and a wide antibacterial spectrum, and the market demand is relatively large. 1-methanesulfonyl-2-imidazolidinone is an intermediate for the preparation of drugs satrinidazole and mezlocillin, and the current synthesis method of 1-methylsulfonyl-2-imidazolidinone is under the action of alkali such as NaH, with 2 -Imidazolidinone and methanesulfonyl chloride are synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/38
Inventor 董川任玉杰董连锁
Owner 上海东满进出口有限公司