Method for synthesizing 4-nitrobenzyl chloroformate

A technology for the synthesis of benzyl p-nitrochloroformate and its synthesis method is applied in the field of synthesis of benzyl p-nitrochloroformate, which can solve the problems of difficult storage and transportation, potential safety hazards, poor thermal stability, etc., and achieve the elimination of production safety. Hidden dangers, reduction in the production of three wastes, and excellent product quality

Inactive Publication Date: 2008-12-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Phosgene is an extremely dangerous and highly toxic gas, which is difficult to measure accurately and poses a safety hazard in industrial production
Benzyl p-nitrochloroformate has poor thermal stability, is easily decomposed, and is not easy to store and transport

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The molar ratio of feeding is p-nitrobenzyl alcohol: bis(trichloromethyl) carbonate: acid-binding agent is 1: 0.4: 0.9, the organic solvent is dichloromethane, and its consumption is 5 times of the quality of p-nitrobenzyl alcohol.

[0016] In a 500mL four-necked flask equipped with a thermometer, a reflux condenser, a constant pressure dropping funnel, and mechanical stirring, add 48g of bis(trichloromethyl)carbonate, an organic solvent and 1g of N,N-dimethylformamide , ice-bath to 0°C-5°C, start stirring, after dissolving, add 61.2g p-nitrobenzyl alcohol, then start to drop 43.5g N,N-dimethylaniline and stir at 0°C-5°C for 4 hours. After the reaction was completed, the reaction solution was slowly added dropwise to 1200 g of petroleum ether, and placed in a freezer for 24 hours. Filtration and vacuum drying yielded 82 g of light yellow benzyl p-nitrochloroformate solid, with a yield of 95%, a purity of 99.5% (HPLC), and a melting point of 31.0°C to 32.0°C.

Embodiment 2

[0018] The feed molar ratio is changed to p-nitrobenzyl alcohol: bis(trichloromethyl)carbonate: acid-binding agent is 1: 0.5: 0.9, and the organic solvent is dichloromethane, and its consumption is 5 times of the p-nitrobenzyl alcohol quality .

[0019] Other conditions and preparation steps were the same as in Example 1, and 82.5 g of benzyl p-nitrochloroformate was obtained as a solid, with a yield of 95.7%. The detected purity is 99.5% (HPLC), and the melting point is 31.0°C to 32.0°C.

Embodiment 3

[0021] The feed molar ratio is changed to p-nitrobenzyl alcohol: bis(trichloromethyl) carbonate: acid-binding agent is 1: 0.8: 0.9, and the organic solvent is dichloromethane, and its consumption is 5 times of the p-nitrobenzyl alcohol quality .

[0022] The preparation steps of other conditions were the same as in Example 1, and 82.8 g of benzyl p-nitrochloroformate was obtained as a solid, with a yield of 96%. The detected purity is 99.5% (HPLC), and the melting point is 31.0°C to 32.0°C.

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Abstract

The invention provides a process for synthesizing 4-Nitrobenzyl chloroformate, which comprises reacting trichloromethyl chloroformate or bis(trichloromethyl)carbonate with p-nitrobenzyl alcohol at -40-20 deg C under the action of acid-binding agent, finally carrying out post-treatment to obtain the outcome yield.

Description

(1) Technical field [0001] The invention relates to a synthetic method of benzyl p-nitrochloroformate. (2) Background technology [0002] Benzyl p-nitrochloroformate is mainly used as a hydroxyl and amino protection reagent for nucleosides, and is widely used in drug synthesis. [0003] Before the present invention was made, the chemical synthesis method of benzyl p-nitrochloroformate was prepared by reacting p-nitrobenzyl alcohol and phosgene as raw materials. For example: JP 2004300052 and J.Am.Chem.Soc., 1952, 74, 3818-3820, etc. Phosgene is an extremely dangerous and highly toxic gas, which is difficult to measure accurately and has potential safety hazards in industrial production. Benzyl p-nitrochloroformate has poor thermal stability, is easily decomposed, and is not easy to store and transport. (3) Contents of the invention [0004] The object of the invention is to provide a kind of easy and simple operation, safe and reliable production, the method for the syn...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/12C07C205/42
Inventor 李永曙苏为科郑志国
Owner ZHEJIANG UNIV OF TECH
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