Process for producing cis-1.3 disubstituted benzyl imidazoline-2-ketone-2H-furo[3.4-d]imidazole-2,4,6- trione

A technology of dibenzyl imidazoline and benzyl imidazoline, applied in the field of organic chemistry, can solve the problems of difficulty in obtaining high-purity products, difficult to complete the reaction, difficult to separate and apply, etc.

Inactive Publication Date: 2008-08-20
FUDAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

U.S. Patent 2489232 describes 1,3-dibenzyl imidazolin-2-one-cis-4,5-dicarboxylic acid and acetic anhydride dehydration ring closure to prepare cis-1.3-dibenzyl imidazolin-2-one-2H - The preparation method of furo[3.4-d]imidazole-2,4,6-trione (cyclic acid anhydride, I), but the reaction conditions and yield are not disclosed, in our research process (Chemical Journal of Chinese Universities, 2001 , 22, 1141), found that 1,3-dibenzylimidazolin-2-ketone-cis-4,5-dicarboxylic acid and acetic anhydride must be reacted at 1:3 in mol ratio, yield 90%, However, there are still 5 to 10% of 1,3-dibenzyl imidazolin-2-one-cis-4,5-dicarboxylic acid raw materials not completely reacted, even if the reaction time is prolonged to 40h,...

Method used

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  • Process for producing cis-1.3 disubstituted benzyl imidazoline-2-ketone-2H-furo[3.4-d]imidazole-2,4,6- trione
  • Process for producing cis-1.3 disubstituted benzyl imidazoline-2-ketone-2H-furo[3.4-d]imidazole-2,4,6- trione
  • Process for producing cis-1.3 disubstituted benzyl imidazoline-2-ketone-2H-furo[3.4-d]imidazole-2,4,6- trione

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Example 1 1,3-dibenzylimidazolin-2-one-cis-4,5-dicarboxylic acid (35.5g, 0.10mol), acetyl chloride (8.56mL, 0.12mol) and toluene (355mL) were placed In the reaction flask, heat and stir to reflux for 1h. The excess acetyl chloride and acetic acid were removed under reduced pressure to obtain white powder I (33.7 g, 99%), mp 236-237°C, content 99.5% (HPLC).

[0017] IR(KBr): v=1805, 1740, 1687, 1227cm -1 . 1 H NMR (CDCl 3 ): δ=4.21(s, 2H, C 3a -H and C 6a -H), 4.19, 5.10 (dd, 4H, J=15Hz, 2×CH 2 C 6 h 5 ), 7.26~7.39 (m, 10H, 2×ArH) ppm.

[0018] EI-MS: (m / z, %)=336 (M + , 13.6), 264(15.6), 173(5.8), 132(10.9), 91(100).

Embodiment 2

[0019] Example 2 1,3-dibenzylimidazolin-2-one-cis-4,5-dicarboxylic acid (35.5g, 0.10mol), acetyl chloride (14.3mL, 0.20mol) and 1,2-bis Ethyl chloride (650mL) was placed in the reaction flask, heated and stirred under reflux for 15h. Cooled to room temperature, precipitated solid, filtered, dried to give white powder I (32g, 95%), mp 235~237℃.IR, 1 H NMR and MS are consistent with the examples.

Embodiment 3

[0020] Example 3 1,3-dibenzylimidazolin-2-one-cis-4,5-dicarboxylic acid (35.5g, 0.10mol), propionyl chloride (17.4mL, 0.20mol) and toluene (710mL) were placed In the reaction flask, heat and stir to reflux for 8h. Cooled to room temperature, precipitated solid, filtered and dried to obtain white powder I (33g, 98%), mp236~236.5℃.IR, 1 H NMR and MS are consistent with the examples.

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Abstract

The invention belongs to the technical field of organic chemistry, and more particularly relates to a preparation method of cis-1.3-disubstituted benzyl imidazoline-2-ketone-2H-furo (3.4-d) imidazole-2, 4, 6-triketone (cyclic anhydride, I). The prior art has the disadvantages of high unit consumption of acetic anhydride, incomplete reaction and poor product quality, etc. In the preparation method, 1, 3-disubstituted benzyl imidazoline-2-ketone-cis-4, 5-dicarboxylic acid and various acyl halide are subject to dehydration/ ring closure in an organic solvent or in a solvent-free way so as to obtain the cis-1.3-disubstituted benzyl imidazoline-2-ketone-2H-furo (3.4-d) imidazole-2, 4, 6-triketone (cyclic anhydride, I). The method can avoid the adoption of a great deal of acetic anhydride, and has mild reaction condition, product purity of more than 99 percent, low cost and less pollution to the environment, thus being suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, in particular to a cis-1.3-disubstituted benzyl imidazolin-2-ketone-2H-furo[3.4-d]imidazole-2,4,6-triketone (cyclic anhydride , 1) preparation method. [0002] [0003] where R 1 for hydrogen, C 1 ~C 6 Alkyl, phenyl, p-tolyl, p-methoxyphenyl, 3,4-dimethylphenyl, 3,4-dimethoxyphenyl, 3,4,5-trimethylphenyl, 3,4,5-trimethoxyphenyl or p-chlorophenyl, Ar is phenyl, p-tolyl, p-methoxyphenyl, 3,4-dimethylphenyl, 3,4-dimethoxy phenyl, 3,4,5-trimethylphenyl, 3,4,5-trimethoxyphenyl, p-chlorophenyl, thienyl, furyl or naphthyl. Background technique [0004] (3aS, 6aR)-1,3-disubstituted benzyl-tetrahydro-4H-furo[3,4-d]imidazole-2,4(1H)-dione (I) is a synthetic d-biotin ( d-Biotin, vitamin H, key intermediate of coenzyme R). U.S. Patent 2489232 describes 1,3-dibenzyl imidazolin-2-one-cis-4,5-dicarboxylic acid and acetic anhydride dehydration ring closure to prepare cis-1.3-dibenzyl imidazol...

Claims

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Application Information

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IPC IPC(8): C07D491/04
Inventor 陈芬儿戴惠芳黄建吴程盛浩熊非
Owner FUDAN UNIV
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