Preparation method for 3-aminomethyltetrahydrofuran

A technology of aminomethyltetrahydrofuran and nitrile tetrahydrofuran, which is applied in the field of preparation of 3-aminomethyltetrahydrofuran, can solve the problems of large pollution, complicated operation, and difficulty in obtaining it, and achieves low pollution to the human body and the environment, simple process operation, and high production efficiency. low cost effect

Active Publication Date: 2017-02-01
CHANGZHOU SUNLIGHT PHARMA
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Problems solved by technology

[0014] The disadvantages of this method are: the price of malic acid is relatively high and it is not easy to obtain, and its catalytic hydrogenation reduction conditions are relatively harsh, and the operation is relatively complicated; in addition, the nucleophilic substitution needs to use highly toxic sodium cyanide, which is more harmful to human body and environment. Large, so it is not suitable for industrialized mass production

Method used

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Embodiment 1）

[0029] The preparation method of the 3-aminomethyltetrahydrofuran of the present embodiment has the following steps:

[0030] ①Add 106.0g of acrylonitrile and 161.0g of 2-chloroethanol into a four-neck flask, add 10.0g of sodium hydroxide in batches under stirring, and keep it at 25±5°C for 2 hours after the addition, and control it in the sampling center to Raw material disappears.

[0031] The solid was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure at a temperature of 50±5°C to obtain 158.6 g of 2-chloroethyl-2-cyanoethyl ether as a colorless oily liquid with a yield of 59.4%.

[0032] ②Add 158.6g of 2-chloroethyl-2-cyanoethyl ether prepared in step ① and 800mL of tetrahydrofuran into a four-necked flask, cool to 0-5°C, add 47.2g of sodium amide in batches, and then heat up to reflux, Insulate the reaction for 6 hours, and control the sampling until the raw materials disappear.

[0033] Stop heating, cool to room temperature (15...

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Abstract

The invention discloses a preparation method for 3-aminomethyltetrahydrofuran. The preparation method comprises the following steps: with acrylonitrile as a starting material, carrying out an addition reaction with 2-halogenated ethyl alcohol so as to obtain an intermediate 2-haloethyl-2-nitrile ethyl ether; then subjecting the intermediate 2-haloethyl-2-nitrile ethyl ether to cyclic condensation so as to obtain an intermediate 3-nitrile tetrahydrofuran; and finally subjecting the intermediate 3-nitrile tetrahydrofuran to catalytic hydrogenation so as to obtain 3-aminomethyltetrahydrofuran. The preparation method provided by the invention has the advantages of cheap and easily-available starting material, short synthetic route, simple process operation, low production cost, little pollution to the human body and the environment, good yield and applicability to large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and in particular relates to a preparation method of 3-aminomethyltetrahydrofuran. Background technique [0002] 3-Aminomethyltetrahydrofuran is a key intermediate for the synthesis of the third-generation nicotinic insecticide dinotefuran (see Japanese patent document JPH07173157A), and is also a key intermediate for other new drugs (see international patent documents WO2015123365A1 and WO2015162456A1) . [0003] At present, the synthetic method of 3-aminomethyltetrahydrofuran mainly contains following three kinds: [0004] (1) Diethyl malonate and ethyl chloroacetate are used as starting materials to produce triethyl 1,2,2-ethanetricarboxylate through nucleophilic substitution reaction under the action of alkaline catalyst sodium ethoxide, Then it is reduced to 2-hydroxymethyl-1,4-butanediol by sodium borohydride, and then 3-hydroxymethyltetrahydrofuran is synthesized by self-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/14
CPCC07D307/14
Inventor 胡锦平胡国宜郑建龙奚小金
Owner CHANGZHOU SUNLIGHT PHARMA
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