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Method for synthesizing α-hydroxyamides by 2-hydroxymalonocyanide

A technology of hydroxymalonocyanide and hydroxyamide, which is applied in the formation/introduction of amide groups, the preparation of carboxylic acid amides, chemical instruments and methods, etc., can solve the problems of high cost, long reaction time, complicated operation and post-treatment, etc. To achieve the effect of short reaction time, clean reaction and high yield

Active Publication Date: 2016-08-10
武汉药明康德新药开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the technical problems of complex operation and post-treatment, long reaction time and high cost in the existing method for synthesizing a-hydroxyamide

Method used

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  • Method for synthesizing α-hydroxyamides by 2-hydroxymalonocyanide
  • Method for synthesizing α-hydroxyamides by 2-hydroxymalonocyanide
  • Method for synthesizing α-hydroxyamides by 2-hydroxymalonocyanide

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Experimental program
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Effect test

Embodiment 1

[0015]

[0016] Benzaldehyde (106 mg, 1 mmol) and methylamino alcohol solution (470 mg, 33% mass fraction, 5 mmol) were dissolved in 2 mL of methanol, and acetic acid solution of 2-hydroxypropanocyanide (5 mL, 1 mol / L) was added, 50 Stir for 10 minutes at °C. The reaction solution was concentrated and separated by column chromatography to obtain α-hydroxyphenylacetamide (139 mg, 84%). 1 H NMR (400 MHz, CD 3 OD)δ 7.43-7.26 (m, 5H), 5.17 (s, 1H), 3.68 (s, 3H).

Embodiment 2

[0018]

[0019] 2-Formaldehyde furan (96 mg, 1 mmol) and methylamino alcohol solution (940 mg, 33% mass fraction, 10 mmol) were dissolved in 2 mL of methanol, and 2-hydroxypropanedicyanide in trifluoroacetic acid solution (0.1 mL, 10 mol / L), stirred at 30°C for 100 minutes. The reaction solution was concentrated and separated by column chromatography to obtain a-hydroxy-2-furacetamide (128 mg, 83%). 1 HNMR (400 MHz, CD 3 OD) δ 8.20-8.15 (m, 1H), 7.55-7.54 (m, 1H), 6.53-6.44 (m, 2H), 5.80 (s, 1H), 3.68 (s, 3H).

Embodiment 3

[0021]

[0022] Trans-cinnamaldehyde (132 mg, 1 mmol) and methylamino alcohol solution (94 mg, 33% mass fraction, 1 mmol) were dissolved in 2 mL of methanol, and acetic acid solution of 2-hydroxypropanedicyanide (0.4 mL, 7.75 mol / L), stirred at 0°C for 120 minutes. The reaction solution was concentrated and separated by column chromatography to obtain trans-methyl 2-hydroxy-3-ene-phenylbutyramide (167 mg, 87%). 1 H NMR (400 MHz, CD 3 OD) δ 7.48 (d, J= 1.2 Hz, 2H), 7.40-7.34 (m, 3H),7.02 (d, J= 15.6 Hz, 1H), 6.18-6.11 (m, 1H), 4.72 (d, J = 9.2 Hz, 1H), 3.87(s, 3H), 2.71 (s, 3H).

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Abstract

The invention relates to synthesis of alpha-oxyamide through reaction of 2-hydroxy propylene cyanide as well as corresponding aldehyde or ketone and amine, which mainly solves the problems that the preparation of common alpha-oxyamide has a plurality of reaction steps, the reaction operation is complicated, the reaction cost is high, the post treatment is a trouble, and the like. According to the method, 2-hydroxy propylene cyanide as well as corresponding aldehyde or ketone and amine are directly mixed, methanol or acetonitrile is taken as the solvent, and the product can be obtained by stirring for 10-120 minutes. The method for synthesizing alpha-oxyamide is safe and efficient.

Description

technical field [0001] The invention relates to a method for synthesizing α-hydroxyamide from 2-hydroxymalonocyanide. Background technique [0002] The chemical synthesis method of common α-hydroxyamide is as follows at present: [0003] The amide is first reacted with acid chloride and hydroxylamine, then reacted with methanesulfonyl chloride, and finally hydrolyzed in acetonitrile and water to obtain the product, as reported in Journal of Organic Chemistry (Journal of Organic Chemistry, 57(21), 5700-7; 1992), reaction The formula is as follows: [0004] [0005] The operation and post-processing of this method are complex, the reaction time is long, and the cost is high. Contents of the invention [0006] The purpose of this invention is to provide a kind of method that takes 2-hydroxy propanedicyanide as raw material synthetic α-hydroxy amides. The method mainly solves the technical problems of complex operation and aftertreatment, long reaction time and high cost...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B43/06C07C231/14C07C235/34C07D307/54C07D213/56C07D207/337C07D277/30C07D239/30
Inventor 张治柳林小娟于海宇吴成德马汝建陈曙辉
Owner 武汉药明康德新药开发有限公司
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