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Process for preparing 1,3-dibenzyl imidazoline-2-ketone-cis-4, 5-dicarboxylic acid (I)
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A technology of dibenzyl imidazoline and dicarboxylic acid, which is applied in 1 field, can solve the problems of high unit consumption of benzylamine, harsh labor protection conditions, etc., and achieve the effects of low cost, easy recycling, and convenient source
Inactive Publication Date: 2004-06-02
FUDAN UNIV
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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.
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[0030] One, the preparation of cis-2,3-dichlorosuccinic acid (II)
example 1
[0031] 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
[0032] 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.
[0033] Two, the preparation of cis-2,3-dibenzylaminosuccinic acid (III)
[0034] 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.
[0035] Example 2 ...
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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) [0002] Background technique [0003] 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 ope...
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