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Method for synthesizing 1-chloroformyl-3-methyl sulfonyl-2-imidazo flavanone

A technology of imidazolidinone and methylsulfonyl, which is applied in the field of synthesis of pharmaceutical intermediates, and can solve the problems of waste of time and raw materials, production constraints, and low reaction yields

Inactive Publication Date: 2010-06-23
YIYUAN XINQUAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, there are problems such as low reaction yield in step (1) and long overall reaction time, resulting in waste of time and raw materials, which greatly restricts actual production.

Method used

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  • Method for synthesizing 1-chloroformyl-3-methyl sulfonyl-2-imidazo flavanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Step (1): Preparation of methylsulfonyl-2-imidazolidinone:

[0031] The molar ratio of feeding is 2-imidazolidinone:methanesulfonyl chloride:triethylamine=1:1.2:0.1.

[0032] Add 2-imidazolidinone and methanesulfonyl chloride into the reaction kettle and stir, react at 10°C for 1h, then heat up to 90°C, when solid matter appears, add catalyst triethylamine, continue to react for 1h, add water, and heat up to All the solid matter was dissolved, cooled to 10°C, suction filtered, washed with water, and dried to obtain the product methanesulfonyl-2-imidazolidinone with a yield of 76%, a melting point of 190.3-190.8°C, a content of 98.6% (HPLC), and a purity of 99.1 %.

[0033] Step (2): Preparation of 1-chloroformyl-3-methylsulfonyl-2-imidazolidinone:

[0034] The molar ratio of feeding is methanesulfonyl-2-imidazolidinone: triphosgene: triethylamine=1:0.4:0.4

[0035] The amount of solvent used: methanesulfonyl-2-imidazolidinone: dichloromethane = 1 g: 5 ml.

[0036] A...

Embodiment 2

[0038] Step (1): Preparation of methylsulfonyl-2-imidazolidinone:

[0039] The molar ratio of feeding is 2-imidazolidinone:methylsulfonyl chloride:pyridine=1:1.2:0.1.

[0040] Add 2-imidazolidinone and methanesulfonyl chloride into the reaction kettle and stir, react at 10°C for 1h, then heat up to 90°C, when solid matter appears, add catalyst pyridine, continue to react for 1h, add water, heat up to solid matter All dissolved, cooled to 10°C, suction filtered, washed with water, and dried to obtain the product methanesulfonyl-2-imidazolidinone with a yield of 80%, a melting point of 190.4-191.0°C, a content of 98.8% (HPLC), and a purity of 99.0%.

[0041] Step (2): Preparation of 1-chloroformyl-3-methylsulfonyl-2-imidazolidinone:

[0042] The molar ratio of feeding is methanesulfonyl-2-imidazolidinone:triphosgene:triethylamine=1:0.4:0.4.

[0043] The consumption of solvent: methylsulfonyl-2-imidazolidinone: dichloromethane=1g: 10ml

[0044] Add the methanesulfonyl-2-imidaz...

Embodiment 3

[0046] Step (1): Preparation of methylsulfonyl-2-imidazolidinone:

[0047] The feeding molar ratio is 2-imidazolidinone: methylsulfonyl chloride: N, N-dimethylformamide = 1: 1.2: 0.1

[0048] Add 2-imidazolidinone and methanesulfonyl chloride into the reaction kettle and stir, react at 10°C for 1 hour, then heat up to 90°C, when solid matter appears, add catalyst N,N-dimethylformamide to continue the reaction 1h, add water, heat up until the solid matter is completely dissolved, cool down to 10°C, filter with suction, wash with water, and dry to obtain the product methanesulfonyl-2-imidazolidinone with a yield of 78%, a melting point of 190.0-190.5°C, and a content of 98.4% (HPLC), 99.3% pure.

[0049] Step (2): Preparation of 1-chloroformyl-3-methylsulfonyl-2-imidazolidinone:

[0050] The molar ratio of feeding is methanesulfonyl-2-imidazolidinone:triphosgene:triethylamine=1:0.4:0.4.

[0051] The consumption of solvent: methylsulfonyl-2-imidazolidinone: dichloromethane=1g:...

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Abstract

The invention provides a method for synthesizing 1-Chloro-formyl-3-methyl sulfonyl-2-imidazo flavanone, which comprises the steps of: (1) reacting methyl chloride and 2 - imidazo flavanone to produce methylsulfonyl-2-imidazo flavanone under the action of a catalyst; and (2) carrying out acylation reaction on the methylsulfonyl-2-imidazo flavanone and triphosgene in an organic solvent in the presence of a catalyst. The invention is technically characterized in that a catalyst is introduced in the step (1), thereby improving the reaction yield, wherein the catalyst can be triethylamine, pyridine, or N,N-dimethylformamide; and the reaction temperature and the dose of the solvent are adjusted in the step (2), thereby shortening the reaction time and reducing energy consumption, wherein the reaction temperature is between 15 DEG C and 25 DEG C, and the dose of the solvent is adjusted according to the ratio of the methylsulfonyl-2-imidazo flavanone to the organic solvent being 1g:5-10 ml.

Description

technical field [0001] The invention belongs to a synthesis method of a pharmaceutical intermediate, in particular to a synthesis method of 1-chloroformyl-3-methylsulfonyl-2-imidazolidinone. Background technique [0002] 1-Chloroformyl-3-methylsulfonyl-2-imidazolidinone, appearance: white crystalline powder, melting point 178°C, unstable, decomposed with water, soluble in hot acetone, slightly soluble in tetrahydrofuran, insoluble in halogenated alkanes, etc. Organic solvents. [0003] 1-Chloroformyl-3-methylsulfonyl-2-imidazolidinone is a pharmaceutical intermediate, mainly used in the synthesis of the third-generation penicillin-mezlocillin and other new antibiotics of nearly twenty kinds. [0004] 1-chloroformyl-3-methylsulfonyl-2-imidazolidinone is synthesized in two steps. The reaction first reacts 2-imidazolidinone with methylsulfonyl chloride to generate methylsulfonyl-2-imidazolidinone, and then form Sulfonyl-2-imidazolidinone reacts with triphosgene to generate th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/38
Inventor 蔡杰周磊陈国伟许京兰杨萍萍
Owner YIYUAN XINQUAN CHEM
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