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One-step method for synthesizing N-methyl-N-methoxyamide

A technology of methoxy amide and methoxy amine, which is applied in the preparation of sulfonic acid amide, organic chemistry, etc., can solve the problems of difficult residues or by-products, expensive deoxidizing and fluorinating agents, and wasteful yield of raw materials. Ease of handling, low synthesis cost, effect of reaction time period

Inactive Publication Date: 2009-08-26
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the deoxidizing fluorinating agent used is relatively expensive, and the residue or by-product after the reaction is difficult to remove from the mixture, resulting in waste of raw materials and low yield

Method used

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  • One-step method for synthesizing N-methyl-N-methoxyamide
  • One-step method for synthesizing N-methyl-N-methoxyamide
  • One-step method for synthesizing N-methyl-N-methoxyamide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The synthesis of embodiment 1, N-methyl-N-methoxybenzamide

[0019] In a 50mL two-neck flask, add 4mL of dichloromethane, cool down to about 0°C, add 1mmol of benzoic acid, 1mmol of triphenylphosphine and 1.1mmol of N-bromosuccinimide under stirring; stir for 10 minutes Then add 1.7mmol of N-methyl-N-methoxylamine, after reacting for 30min, add NaHCO 3 The saturated solution was quenched for 30 min, and the organic phase was separated; the aqueous phase was extracted with dichloromethane, and the anhydrous MgSO 4 Drying, column chromatography to obtain the target compound - N-methyl-N-methoxybenzamide. The yield was 81%.

[0020] Its reaction formula is as follows:

[0021]

[0022] Target compound N-methyl-N-methoxybenzamide by IR, 1 HNMR, 13 CNMR detects that its product is a pure target compound, and the data are as follows:

[0023] IRv(neat) / cm -1 3061, 2968, 2933, 2819, 1644, 1576, 1451, 1416, 1377, 1213, 982, 787, 707;

[0024] 1 H NMR (400MHz, CDCl ...

Embodiment 2

[0026] Embodiment 2, the synthesis of N-methyl-N-methoxyl group-2-(N-p-methylbenzenesulfonyl) phenylpropanamide

[0027] In a 50mL two-necked flask, add 4mL tetrahydrofuran, cool down to about 0°C, and mix 1mmol (N-p-toluenesulfonyl)phenylpropionic acid, 1mmol triphenylphosphine and 1.1mmol N-bromobutylene under stirring Add imide; stir for 10 minutes, add 1.7mmol of N-methyl-N-methoxyamine, react for 1h, add NaHCO 3 The saturated solution quenched the reaction for 30 min; the organic phase was separated, the aqueous phase was extracted with dichloromethane, anhydrous MgSO 4 Drying and column chromatography yielded the target compound—N-methyl-N-methoxy-2-(N-p-methylbenzenesulfonyl)phenylpropanamide. The yield was 88%.

[0028] Its reaction formula is as follows:

[0029]

[0030] The target compound N-methyl-N-methoxy-2-(N-p-methylbenzenesulfonyl) phenylpropanamide was subjected to IR, 1 HNMR 13 CNMR detection, its product is a pure product, the data is as follows:

...

Embodiment 3

[0034] Embodiment 3: the synthesis of N-methyl-N-methoxy-3,5,5-trimethylhexanamide

[0035] Steps: In a 50mL two-neck flask, add 4mL tetrahydrofuran, cool down to about 0°C, stir 1mmol 3,5,5-trimethylhexanoic acid, 1mmol triphenylphosphine and 1.1mmol N-bromobutanedi Add imide to it; stir for 10 minutes, add 1.7mmol of N-methyl-N-methoxyamine, react for 3h, add NaHCO 3 The saturated solution was quenched for 30 min, the organic phase was separated, the aqueous phase was extracted with dichloromethane, anhydrous MgSO 4 Drying and column chromatography gave the target compound - N-methyl-N-methoxy-3,5,5-trimethylhexanamide. The yield was 99%. Its reaction formula is as follows:

[0036]

[0037]The target compound N-methyl-N-methoxy-3,5,5-trimethylhexanamide by IR, 1 HNMR, 13 CNMR detection, its product is a pure product, the data is as follows:

[0038] IR v(neat) / cm -1 3319, 2955, 2934, 1668, 1465, 1412, 1379, 1247, 1177, 1116, 1004, 940;

[0039] 1 H NMR (400MHz, ...

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Abstract

The invention provides a one-step method for synthesizing N-methyl-N-methoxyamide, comprising the steps of: taking methylene dichloride or tetrahydrofuran as a solvent, reacting carboxylic acid with triphenylphosphine, N-bromosuccimide and N-methyl-N-methoxyamine to generate relevant N-methyl-N-methoxyamide. The invention is simple in reaction procedure, easily-available in raw materials, mild in reaction conditions, environmentally-friendly, low in synthesis cost, high in efficiency and yield and easy in after treatment as well as can efficiently synthesize various chiral or achiral N-methyl-N-methoxyamide.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a synthesis method of N-methyl-N-methoxyamide, in particular to a method using dichloromethane or tetrahydrofuran as a solvent, using carboxylic acid and triphenylphosphine, N- A method for synthesizing the corresponding N-methyl-N-methoxyamide in one step through the action of bromosuccinimide and N-methyl-N-methoxyamine. Background technique [0002] N-methyl-N-methoxyamides (hereinafter referred to as Weinreb amides) are a very important class of acylating reagents, which have been widely used in the synthesis of natural product active substances. Such amides differ from other amides in that when reacted with metalorganic reagents such as Grignard reagents, ketones are formed rather than alcohols. Weinreb amides are also readily reduced to aldehydes by metal hydrides. It is worth emphasizing that the configuration of optically active Weinreb amides does not change wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C259/10C07C311/16C07C259/06C07C303/40
Inventor 胡雨来张正臣黄丹凤徐长明
Owner NORTHWEST NORMAL UNIVERSITY
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