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Method for synthesizing 3-aminomethyl tetrahydrofuran by taking furan as raw material

A technology of aminomethyltetrahydrofuran and nitromethyl, which is applied in the field of synthesizing 3-aminomethyltetrahydrofuran, can solve the problems of unsuitability for industrial production, long synthesis route and high total yield, and achieves low raw material price and low production cost , the effect of short synthetic route

Active Publication Date: 2019-06-07
HUBEI YUANDA FUCHI PHARMA CHEM
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The fifth is to use 3-hydroxymethyl tetrahydrofuran as a raw material, react with methanesulfonyl chloride to generate 3-methylsulfonyloxymethyl tetrahydrofuran, and then undergo two-step reaction ammoniation to obtain 3-aminomethyl tetrahydrofuran (EP 0649845, WO2005066126). The synthesis route of the method is long, and the total yield is low, thereby is not suitable for industrial production
The method has mild conditions and high overall yield, but it is not very economical when measured from the molecular weight (144.13) of the raw material and the molecular weight of the product (101.15).

Method used

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  • Method for synthesizing 3-aminomethyl tetrahydrofuran by taking furan as raw material
  • Method for synthesizing 3-aminomethyl tetrahydrofuran by taking furan as raw material

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Experimental program
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Embodiment 1

[0034] Preparation of TS-1 catalyst for synthesis of 1,4-butenedialdehyde by oxidative ring opening of furan.

[0035] According to US Patent 4410501, 455 grams of tetraethyl silicate are placed in a single-necked flask equipped with a stirrer and kept in a carbon dioxide-free state, 15 grams of titanium (IV) tetraethoxide are added, and then 800 grams of 25% by weight are gradually added Tetrapropylammonium hydroxide solution (without inorganic base). The mixture was stirred for about 1 hour, and then heating was started carefully to accelerate the hydrolysis and evaporate the liberated ethanol. After about 5 hours at 80-90°C, the ethanol has completely evaporated to dryness. The volume was increased to 1.5 liters with distilled water, and the milky white homogeneous solution was transferred to an autoclave equipped with a stirrer. The mixture was heated to 175°C and kept stirring at this temperature under its own pressure for 10 days. Then the autoclave is cooled, the reacti...

Embodiment 2

[0037] Synthesis of 1,4-butenedialdehyde.

[0038] 300 ml of acetonitrile, 21.0 g (0.30 mol) of furan, TS-1 (3 g) and hydrogen peroxide (35%, 0.36 mmol) were added to a 1000 ml single-necked flask. The mixture was stirred at room temperature for 2 hours, at which time the peroxide disappeared (detected with saturated potassium iodide aqueous solution). 200 ml of water was added to the reaction, the aqueous layer was extracted three times with dichloromethane, the organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to obtain the product 1,4-butenedialdehyde, which was directly used in the next step 2-nitromethyl -1,4-Butanedialdehyde synthesis reaction. 1 H NMR(400MHz, CDCl 3 )δ9.70 (m, 2H), 7.70-7.66 (m, 2H).

Embodiment 3

[0040] Synthesis of 2-nitromethyl-1,4-butanedialdehyde.

[0041] Add proline (1.15g, 0.01mol) to nitromethane (54g, 0.9mol), then add the 1,4-butenedialdehyde obtained above, stir at room temperature for 12h, and then add 100ml of ice water , Extracted with ether three times, 100 ml each time, combined the organic layers, dried and concentrated to obtain the product 2-nitromethyl-1,4-butanedialdehyde directly used in the next step 2-nitromethyl-1,4- Synthesis of butanediol.

[0042] NMR (400MHz, CDCl 3 )δ9.70(s,2H),4.70-4.66(d,J=8.0Hz,2H),2.71-2.65(m,1H), 2.50-2.41(m,2H),2.37-2.30(m,1H) .

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Abstract

The invention discloses a method for synthesizing 3-aminomethyl tetrahydrofuran by taking furan as a raw material, and relates to the technical field of pesticide intermediate synthesis. The method comprises the following five steps: carrying out oxidation and ring opening to obtain 1,4-butene dialdehyde, carrying out Michael addition on the 1,4-butene dialdehyde with nitromethane, carrying out reduction with sodium borohydride, carrying out dehydration cyclization and carrying out catalytic hydrogenation to obtain the 3-aminomethyl tetrahydrofuran. The invention provides the method for synthesizing 3-aminomethyl tetrahydrofuran by taking furan as a raw material. The method is low in raw material price, short in synthesis route and low in production cost, and is suitable for large-scale production.

Description

Technical field [0001] The invention relates to the technical field of pesticide intermediate synthesis, in particular to a method for synthesizing 3-aminomethyltetrahydrofuran using furan as a raw material. Background technique [0002] 3-Aminomethyltetrahydrofuran is an important intermediate in the synthesis of the third generation nicotine insecticide dinotefuran (CN108424406). Its synthesis mainly has the following methods: [0003] One is using 2,3-dihydrofuran as a raw material and reacting with dichloroacetyl chloride to generate 2,3-dihydro-4-dichloroacetylfuran, and then 3-trichloroacetylfuran is obtained under the action of NBS , Then react with ammonia water to produce furan-3-carboxamide, then reduce with LiAlH4 to obtain furan-3-methylamine, and finally undergo Pd / C catalytic hydrogenation reduction to obtain 3-aminomethyltetrahydrofuran (J.Agric.Food Chem.2007, 55,3011-3017), the total yield is 41%, but due to the large amount of tetrahydrolithium aluminum used in ...

Claims

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Application Information

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IPC IPC(8): C07D307/14
Inventor 雷大有杨尚金杨长云叶秀旭谢国范
Owner HUBEI YUANDA FUCHI PHARMA CHEM
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