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Chemically synthetic method for N-chloroformyl imino dibenzyl

A technology of chloroformyl imino dibenzyl and imino dibenzyl, which is applied in the field of chemical synthesis of N-chloroformyl imino dibenzyl, can solve the problem of low product yield and product quality, and inability to react with phosgene. Complete quantification, high requirements for reaction equipment, high yield and purity, solving the problem of tail gas absorption, and avoiding difficult storage effects

Inactive Publication Date: 2007-04-11
ZHEJIANG UNIV OF TECH
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  • Abstract
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Problems solved by technology

Before the present invention provides, the chemical synthesis method of relevant N-chloroformyl imidodibenzyl is mainly phosgene method, and highly toxic phosgene has brought very big potential safety hazard and environmental disaster to production, and gaseous The phosgene reaction cannot be completely quantified, the reaction conditions are harsh, the requirements for the reaction equipment are high, and the product yield and product quality are low

Method used

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  • Chemically synthetic method for N-chloroformyl imino dibenzyl

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Embodiment 1

[0019] The molar ratio of the feed material is iminodibenzyl:trichloromethyl chloroformate:catalyst is 1.0:0.75:0.05, wherein the catalyst is pyridine, the organic solvent is tetrahydrofuran, and its consumption is 8 times of the mass of iminodibenzyl.

[0020] In a 250mL three-neck flask with mechanical stirring, reflux condenser (with tail gas absorption device), and a thermometer, add 19.26g (100mmol) of iminodibenzyl, 14.85g (75mmol) of trichloromethyl chloroformate, and catalyst pyridine 0.395g (5mmol) and 154g tetrahydrofuran (8 times the mass of iminodibenzyl), start mechanical stirring, all solids dissolve, heat to THF reflux temperature, react for 12 hours, monitor the reaction process with HPLC during the reaction (mobile phase: Acetonitrile:water:tetrahydrofuran=40:50:10, C18 silica gel column, flow rate 1.0mL / min). After the reaction, part of the solvent was distilled off under normal pressure to obtain a saturated solution, cooled and crystallized to obtain an off...

Embodiment 2

[0022] The molar ratio of the feed material is iminodibenzyl:trichloromethyl chloroformate:catalyst is 1.0:0.65:0.05, wherein the catalyst is pyridine, the organic solvent is tetrahydrofuran, and its consumption is 8 times of the mass of iminodibenzyl.

[0023] The reaction temperature was reflux temperature, and the reaction time was 15 hours. Other operations were the same as in Example 1 to obtain 25.0 g of N-chloroformyliminodibenzyl, with a product yield of 97.0% and a purity of 99.1%.

Embodiment 3

[0025] The molar ratio of the feed material is dibenzyl imino:trichloromethyl chloroformate:catalyst is 1.0:0.50:0.05, wherein the catalyst is pyridine, the organic solvent is tetrahydrofuran, and its consumption is 8 times of the quality of dibenzyl imino.

[0026] The reaction temperature was reflux temperature, and the reaction time was 15 hours. Other operations were the same as in Example 1 to obtain 24.8 g of N-chloroformyliminodibenzyl, with a product yield of 96.4% and a purity of 98.9%.

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Abstract

The chemical synthesis process of N-chloroformyl imino dibenzyl includes reaction of imino dibenzyl and trichloromethyl chloroformate as materials in organic solvent at 20-150 deg.c in the action of organic amine catalyst for 2-20 hr; and cooling to crystallize. The material includes imino dibenzyl, trichloromethyl chloroformate and organic amine catalyst in the weight ratio of 1.0 to 0.5-3.0 to 0.001-2.0, and organic solvent in 0.5-20 times the weight of imino dibenzyl. Trichloromethyl chloroformate is one kind of organic reagent with low toxicity, high efficiency and good reaction performance. The chemical synthesis process of the present invention is advanced, and has high yield, product purity and excellent industrial application foreground.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of N-chloroformyl imidodibenzyl. (2) Background technology [0002] N-chloroformyl imidodibenzyl is an important pharmaceutical intermediate for the synthesis of carbamazepine and oxcarbazepine. Before the present invention provides, the chemical synthesis method of relevant N-chloroformyl imidodibenzyl is mainly phosgene method, and highly toxic phosgene has brought very big potential safety hazard and environmental disaster to production, and gaseous The phosgene reaction cannot be completely quantified, the reaction conditions are harsh, the requirements for the reaction equipment are high, and the product yield and product quality are relatively low. (3) Contents of the invention [0003] The purpose of the present invention is to provide a simple and reasonable process, high safety, effective utilization of by-products, high reaction yield, high product purity, low production cost, and ba...

Claims

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Application Information

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IPC IPC(8): C07D223/22
Inventor 苏为科李坚军翁意意
Owner ZHEJIANG UNIV OF TECH
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