59564-78-2

Basic information

• Product Name: 1,3-Bisbenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid
• Synonyms: 1,3-DIBENZYL IMIDAZOLIDINONE-4,5-DICARBOXYLIC ACID;1,3-BISBENZYL-2-OXOIMIDAZOLIDINE-4,5-DICARBOXYLIC ACID;1,3-Dibenzyl-2-Imidaxzolidone-Cis-4,5-Dicarboxylic Acid;Vitamin H intermediates Cyclic acid;1,3-BISBENZYL-2-OXOIMIDAZOLIDINE-4,5-DI&;CYCLIC ACID;1,3-Dibenzyl-2-imidax zolidone-cis-4,5-dicarboxylic;1,3-Bisbenzyl-2-oxoi
• CAS NO: 59564-78-2
• Molecular Formula: C₁₉H₁₈N₂O₅
• Molecular Weight: 354.36
• EINECS: 261-806-8
• Product Categories: Organic acids;Heterocyclic Compounds;(intermediate of d-biotin);Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines
• Mol File: 59564-78-2.mol

Chemical Properties

• Melting Point: 170-174 °C(lit.)
• Boiling Point: 654.2 °C at 760 mmHg
• Flash Point: 349.5 °C
• Appearance: /
• Density: 1.426 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.74±0.40(Predicted)
• CAS DataBase Reference: 1,3-Bisbenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bisbenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid(59564-78-2)
• EPA Substance Registry System: 1,3-Bisbenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid(59564-78-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 59564-78-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3-Bisbenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid is used as a building block in organic synthesis for constructing more complex molecules. Its structural complexity and functional groups make it a valuable component in the synthesis of advanced organic compounds.
Used in Pharmaceutical Industry:
1,3-Bisbenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid is used as a pharmaceutical compound for its antifungal and antibacterial properties. Its potential in treating infections caused by fungi and bacteria makes it a candidate for further research and development in the pharmaceutical sector.
Used in Metal Ion Coordination Chemistry:
1,3-Bisbenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid is used as a chelating agent in metal ion coordination chemistry. Its carboxylic acid functional groups can form complexes with metal ions, which may have applications in various chemical processes and technologies. Further research is required to fully understand its capabilities and optimize its use in this field.

InChI:InChI=1/C19H18N2O5/c22-17(23)15-16(18(24)25)21(12-14-9-5-2-6-10-14)19(26)20(15)11-13-7-3-1-4-8-13/h1-10,15-16H,11-12H2,(H,22,23)(H,24,25)

Upstream product

• 1885-14-9 phenyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 40222-70-6 1,3-dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid anhydride 

Relevant articles and documents

Method for pipelined synthesis of vitamin H intermediate

The invention provides a method for pipelined synthesis of a vitamin H intermediate. Specifically, the method comprises the following steps: (1) providing a salt solution of a compound as shown in a formula 2, a triphosgene (BTC) solution and a potassium hydroxide solution; (2) mixing a salt solution of the compound shown in the formula 2, a triphosgene (BTC) solution and a potassium hydroxide solution, and continuously feeding the obtained mixed solution into a pipeline reactor for reaction; and (3) adjusting the pH value of the reaction liquid after the reaction to be acidic to obtain a compound as shown in a formula 3, wherein the salt is potassium salt and/or sodium salt of a compound shown in a formula 2. The method is high in raw material conversion rate, very safe to operate and suitable for industrial production of the vitamin H intermediate.

Preparation method of cis-1, 3-dibenzylimidazole-2-one-4, 5-dicarboxylic acid

The invention discloses a preparation method of cis-1, 3-dibenzylimidazole-2-one-4, 5-dicarboxylic acid. The preparation method comprises dissolving a compound 1 shown in the formula 1, a phosphate, anitrogen oxide compound and an oxidation aid in an organic solvent, carrying out a reaction process at 10-60 DEG C for 4-10h to obtain a compound 2 shown in the formula 2, dissolving the compound 2 in water, adding an alkaline substance into the solution, and carrying out a reaction process at 10-50 DEG C for 2-8h to obtain a compound 3 shown in the formula 3. The preparation method has a simpleroute, utilizes cheap and easily available 1, 3-dibenzyl-4-hydroxymethyl-5-methoxycarbonylimidazolium-2-one as a starting material and produces a desired product biotin intermediate namely cis-1, 3-dibenzylimidazole-2-one-4, 5-dicarboxylic acid through the two-step reaction. The reaction conditions are mild, operation is simple, a yield is high, chemical selectivity is good, a production cost is low, the preparation method is suitable for industrial production and the large practical application value and social and economic benefits are obtained.

Process for preparing biotin

The present invention is directed to a process for the production of 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid and of 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid anhydride, starting from meso-2,3-bis(benzylamino)succinic acid dialkali metal salt. The process involves reacting meso-2,3-bis(benzylamino)succinic acid dialkali metal salt with phenyl chloroformate in a monophasic solvent system consisting of an about 2:1 to 1:1 mixture of a water-miscible ether and an aqueous alkali metal hydroxide solution, at a temperature not exceeding about 40° C. The resulting 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid dialkali metal salt is converted, by acidification, into the desired 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid, which is then either isolated, or converted, by heating with acetic anhydride, in an aromatic hydrocarbon as the organic solvent, into the desired 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid anhydride, which is in turn, isolated. Each product is an important intermediate in the multi-stage process for the manufacture of biotin (vitamin H).