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Process for preparing 1,3-dibenzyl imidazoline-2-ketone-cis-4, 5-dicarboxylic acid (Ôàá)

A technology of dibenzyl imidazoline and dicarboxylic acid, which is applied in 1 field, can solve the problems of high unit consumption of benzylamine and strict labor protection conditions, and achieve the effects of low cost, easy recovery, and mild reaction conditions

Inactive Publication Date: 2003-08-06
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process has a high unit consumption of benzylamine, uses a large amount of highly toxic phosgene, requires harsh labor protection conditions, and a large amount of phosgene transportation and process operations have brought a series of problems to be solved for manufacturers who do not produce phosgene themselves.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0026] One, the preparation of cis-2,3-dichlorosuccinic acid (II)

example 1

[0027] Example 1 Fumaric acid (116g, 1.0mol), 30% hydrochloric acid (400mL) is put in the reaction flask, after heating and stirring to reflux, feed chlorine gas to the end point (GC-MS tracking reaction II content reaches more than 97.5%, fumaric acid The peak of the acid raw material disappears), and the passage is completed within 4 hours, and the stirring is continued for 0.5 hours. After the reaction is complete, cool to 5°C. The solid was precipitated, filtered, washed with water, and dried to obtain white powder II (168.3 g, 90%), mp 217-219°C.

example 2

[0028] Example 2 Put fumaric acid (116g, 1.0mol), 40% hydrobromic acid (350mL) in a reaction flask, and at 65° C., feed chlorine gas rapidly to the end point under stirring (the content of GC-MS tracking reaction II reaches 98% Above), pass through within 2h, continue to insulate and stir for 2h. After the reaction is complete, cool to 5-10°C. The solid was precipitated, filtered, washed with water, and dried to obtain white powder II (159 g, 85%), mp 216-219°C.

[0029] Two, the preparation of cis-2,3-dibenzylaminosuccinic acid (III)

[0030] Example 1 II (18.7g, 0.1mol), benzylamine (32.1g, 0.30mol), triethylbenzyl ammonium chloride (0.7g, 0.003mol), anhydrous potassium carbonate (28.9g, 0.21mol) and toluene (200mL) was placed in a dry reaction bottle, stirred and refluxed at 45°C for 5h. After cooling to room temperature, water (200 mL) was added to precipitate a solid, which was filtered and dried to obtain white powder III (29.6 g, 90%), mp220-224.

[0031] Example 2 ...

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PUM

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Abstract

The present invention provides a method for preparing 1,3-dibenzylimidazoline-2-ketone-cis-4,5- dicarboxylic acid, and is characterized by that it utilizes chlorine gas to make fumaric acid produce electrophilic addition reaction to obtain meso-2,3-dichlorosuccinic acid, in the pressence of phase transfer catalyst the meso-2,3-dichlorosuccinic acid and benzylamine are undergone the processes of benzylamination reaction in the solvent so as to synthesize cis-2,3-dibenzylamine succinic acid, the latter and solid carbonyl chloride and undergone the process of phase transfer catalytic ring-closing reaction in the potassium hydroxide solution so as to obtain the invented product. Its total yield rate is up to 74%.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and is a preparation method of 1,3-dibenzyl imidazolin-2-one-cis-4,5-dicarboxylic acid (cyclic acid, I) Background technique [0002] 1,3-dibenzyl imidazolin-2-one-cis-4,5-dicarboxylic acid (I) is an important intermediate for the synthesis of d-biotin (d-Biotin, vitamin H, coenzyme R), foreign literature Such as U.S. Patent 2489232, 4659837, Japanese Patent 60-152469, 59-59668, etc. all describe the preparation of meso-2,3-dibromosuccinic acid and benzylamine in ethanol with fumaric acid as the starting material. A method for converting benzyl amination into meso-2,3-bis(benzylamino)succinic acid, and then performing phosgene ring closure with phosgene to synthesize cyclic acid (I). This process has high unit consumption of benzylamine, the use of a large amount of highly toxic phosgene, harsh labor protection conditions, and a large amount of phosgene transportation and process operations ha...

Claims

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Application Information

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IPC IPC(8): C07C53/15C07C227/16C07C229/34C07D233/30
Inventor 陈芬儿
Owner FUDAN UNIV
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