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Delta-aminoalkylbenzofuranol ethers, and preparation method and application thereof

A technology of aminoalkyl furan phenol ether and aminobutyl furan phenol ether is applied in the field of compound preparation, and can solve the problems of harsh reaction conditions, high reaction temperature, difficult preparation and the like

Active Publication Date: 2018-01-05
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But 2-bromo-1-chloroethane is difficult to obtain, and the price is expensive; and the reaction temperature of the generated 2-chloroethylfuranphenol ether and the potassium salt of phthalimide is high, and the reaction conditions are harsh

Method used

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  • Delta-aminoalkylbenzofuranol ethers, and preparation method and application thereof
  • Delta-aminoalkylbenzofuranol ethers, and preparation method and application thereof
  • Delta-aminoalkylbenzofuranol ethers, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of N-(2-bromoethyl)phthalimide

[0023]

[0024] 3.0g of phthalimide and 30mL of ethanol, magnetically stirred, slowly added dropwise to 10mL of ethanol containing 1.71g of KOH, after dropping, reflux, TLC detected that the reaction of the raw materials was complete, reacted for 2.0h, cooled, filtered with suction, and dried The potassium salt of phthalimide was obtained as a white solid with a yield of 90.3%.

[0025] 50mLDMF, 0.025mol potassium salt of phthalimide, 0.10mol 1,2-dibromoethane, 0.5g TBAB, react at 70°C for 2.0h; cool to room temperature, pour into ice water, extract with ethyl acetate, After washing with water, drying, desolvation, and standing overnight, 5.11 g of colorless solid N-(2-bromoethyl)phthalimide was precipitated; m.p.80-83°C, yield 80.5%.

Embodiment 2

[0027] Preparation of N-(2-hydroxyethyl)phthalimide

[0028]

[0029] Put 0.034mol of phthalic anhydride in a three-necked flask, add dropwise 0.034mol of ethanolamine at room temperature, reflux for 0.5h, cool, precipitate solid, recrystallize to obtain white solid N-(2-hydroxyethyl)phthalimide 5.71 g, m.p.127~129°C, yield 89.8%.

Embodiment 3

[0031] Preparation of N-(2-bromoethyl)phthalimide

[0032]

[0033] 2.60mmol N-(2-hydroxyethyl)phthalimide, 2.60mmol PBr 3 , refluxed for 0.5h, TLC detection was completed, cooled, poured into ice water, and a solid was precipitated, and the crude product was recrystallized from absolute ethanol to obtain a white solid 0.586g N-(2-bromoethyl)phthalimide, m.p. 81-84°C, yield 88.1%.

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PUM

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Abstract

The invention relates to delta-aminoalkylbenzofuranol ethers represented by chemical structural formula I shown in the description, and an application thereof in the preparation of herbicides. In thechemical structural formula I, R is selected from C1-C2 alkyl groups, and n is selected from 2, 3 and 4.

Description

technical field [0001] The invention relates to a preparation method of a class of compounds, in particular to a preparation method and application of δ-aminoalkylfuranphenol ether. Background technique [0002] N-(2-bromoethyl)phthalimide, N-(2-bromopropyl)phthalimide, 2-[2-(2,2-dimethyl-2, 3-Dihydrobenzofuran-7-oxyl)ethyl]isoindoline-1,3-dione, 2-[3-(2,2-dimethyl-2,3-dihydrobenzo Furan-7-oxy)propyl]isoindoline-1,3-dione, 2-(2,2-dimethyl-2,3-benzofuran-7-oxyl)ethylamine and its It has been reported as a pharmaceutical chemical intermediate, such as Stephane Cuisiat et al. [J Med Chem, 2007,50 (4): 865-875] described compound A which has inhibitory activity on dopamine D2 receptors, wherein furanol was used as raw material to prepare 2-Chloroethylfuran phenol ether, and then react with the potassium salt of phthalimide to obtain 2-(2-(2,2-dimethyl-2,3-dihydrobenzofuran-7- Oxygen) ethyl) isoindoline-1,3-dione is obtained intermediate 2-aminoethyl furanol ether by aminolysi...

Claims

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Application Information

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IPC IPC(8): C07D307/86A01N43/12A01P13/00
Inventor 胡艾希杨子辉李静雯
Owner HUNAN UNIV
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