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Synthesis method for 3-aminomethyl tetrahydrofuran

A technology of aminomethyltetrahydrofuran and cyanotetrahydrofuran, which is applied in the field of synthesis of 3-aminomethyltetrahydrofuran, can solve problems such as high technical requirements, unfavorable industrialization, and harsh conditions, and achieve simple process, green method, and industrialization Effect

Pending Publication Date: 2020-06-19
安徽中羰碳一工业技术有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] Although the starting materials of this method are simple and easy to obtain, the reaction needs to be controlled under low temperature and dry conditions, the conditions are harsh, and the amount of organic strong base catalyst used is relatively large, which increases the production cost and is not conducive to industrialization.
[0018] Therefore, it is particularly urgent to solve defects such as poor process safety, high technical requirements, high cost, and low yield in the current synthetic production of 3-aminomethyltetrahydrofuran

Method used

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  • Synthesis method for 3-aminomethyl tetrahydrofuran
  • Synthesis method for 3-aminomethyl tetrahydrofuran
  • Synthesis method for 3-aminomethyl tetrahydrofuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] A kind of synthetic method of 3-aminomethyltetrahydrofuran, specifically comprises the steps:

[0056](1) Ammonium chloride (5.35g, 0.1mol), 2,5-dihydrofuran (7.01g, 0.1mol), palladium dichloride (0.0177g, 0.0001mol) were added to 20mL of N-methylpyrrolidone Then put it into a high-pressure reactor, replace the air in the reactor with carbon monoxide, fill it with carbon monoxide (0.1MPa) after three replacements, stop the reaction after reacting in an oil bath at 200°C for 24 hours, evaporate the solvent to dryness, and weigh it with ethanol Crystallization obtained 7.63 g of an off-white solid, namely 3-formamide tetrahydrofuran, with a purity of 95% and a yield of 63%;

[0057] (2) Dissolve the off-white solid (6.06g, 0.05mol of 3-formamide tetrahydrofuran) obtained in step (1) in toluene (50mL), then add phosphorus pentachloride (10.41g, 0.05mol), and Stir for 20 minutes, then heat up to 50°C and stir for 30 minutes. After the reaction is complete, wash with 10 mL ...

Embodiment 2

[0062] A kind of synthetic method of 3-aminomethyltetrahydrofuran, specifically comprises the steps:

[0063] (1) Add ammonium chloride (107g, 2mol), 2,5-dihydrofuran (14.02g, 0.2mol), palladium acetate (4.49g, 0.02mol) into 40mL of tetrahydrofuran, and then put it into the autoclave In the process, replace the air in the reactor with carbon monoxide, and after three replacements, fill it with carbon monoxide (10MPa), react in an oil bath at 50°C for 24 hours, then stop the reaction, evaporate the reaction solution to dryness, and recrystallize with ethanol to obtain off-white 15.73 g of solid, namely 3-formamide tetrahydrofuran, with a purity of 95% and a yield of 65%;

[0064] (2) The off-white solid (6.06g, 0.05mol of 3-formamide tetrahydrofuran) obtained in step (1) was dissolved in diphenyl ether (50mL), and then dibutyltin oxide (1.245g, 0.005mol) was added, Heat to 200°C for 1.5h until no water is distilled off, filter while hot to remove dibutyltin oxide, concentrate ...

Embodiment 3

[0067] A kind of synthetic method of 3-aminomethyltetrahydrofuran, specifically comprises the steps:

[0068] (1) Ammonium bromide (48.98g, 0.5mol), 2,5-dihydrofuran (14.02g, 0.2mol), sodium chloropalladate (2.942g, 0.01mol) were added to 40mL of N,N-dihydrofuran Methylformamide, then put it into a high-pressure reactor, replace the air in the reactor with carbon monoxide, after three replacements, fill it with carbon monoxide (3MPa), react in an oil bath at 100°C for 24 hours, stop the reaction, and distill under reduced pressure , collect the required fractions and recrystallize with ethanol after cooling to obtain 15.75 g of off-white solid, which is 3-formamide tetrahydrofuran, with a purity of 95% and a yield of 65%;

[0069] (2) Dissolve the off-white solid (4.24g, 0.035mol of 3-formamide tetrahydrofuran) obtained in step (1) in toluene (50mL), then add phosphorus oxychloride (9.79mL, 0.105mol) and di Aluminum (0.036g, 0.00035mol) was heated to reflux for 2h until no wa...

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Abstract

The invention provides a synthetic method for 3-aminomethyl tetrahydrofuran. A target product, namely the 3-aminomethyl tetrahydrofuran is prepared by taking 2,5-dihydrofuran as an initial raw material. In the whole synthesis process, the synthesis method has the advantages of green and environmentally-friendly used raw materials, mild and conveniently-controllable reaction conditions, safe production, low risk, simple process, high yield, and more applicability to industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 3-aminomethyltetrahydrofuran. Background technique [0002] Dinotefuran is the latest generation of neonicotinoid insecticides, and its chemical structure is as follows: [0003] [0004] Compared with traditional neonicotinoid insecticides, tetrahydrofuranyl replaces the previous chloropyridyl and chlorothiazolyl in structure, making it more water-soluble, with a wider insecticidal range and longer efficacy period. long, so the market prospect is broad. [0005] 3-Aminomethyltetrahydrofuran is an important intermediate in the industrial production of dinotefuran, and there are many methods for synthesizing 3-aminomethyltetrahydrofuran reported in the existing literature. [0006] For example, the method of synthesizing 3-aminomethyltetrahydrofuran commonly used in the actual production of factories refers to the method of preparing 3-hydr...

Claims

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Application Information

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IPC IPC(8): C07D307/14C07D307/24
CPCC07D307/14C07D307/24
Inventor 刘显伟马青松马心旺孙东艳魏力璟苏建刘娇
Owner 安徽中羰碳一工业技术有限责任公司
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