Preparation method of amide compound

A technology of dehydration and condensation of amide compounds, applied in the preparation of organic compounds, carboxylic acid amide preparation, chemical instruments and methods, etc., can solve the problems of high cost of coupling reagents, many chemical wastes, cumbersome procedures, etc., and achieve easy separation Purification, broad substrate range, and simple operation

Pending Publication Date: 2022-01-11

WUHAN UNIV OF TECH

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AI-Extracted Technical Summary

Problems solved by technology

However, the existing methods have problems such as high cost of coupling reagents, a lot of chemical waste, cumbersome procedures in industrial production, and difficult purification....

Abstract

The invention relates to a preparation method of an amide compound. The method comprises the following steps: by taking amine and carboxylic acid as raw materials and bromomethylsulfonyl fluoride as a coupling reagent, carrying out dehydration condensation reaction in the presence of alkali and a solvent, and finally separating and purifying to obtain the amide compound. The preparation method has the characteristics of simplicity in operation, low preparation cost, easiness in separation and purification of products and the like, is wide in substrate range, can be used for condensation of amino acids and synthesis and modification of bioactive molecules, and is expected to be used for large-scale synthesis of amides.

Application Domain

Carbamic acid derivatives preparationOrganic compound preparation +1

Technology Topic

Sulfonyl fluorideCoupling reagent +9

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Examples

Experimental program(5)

Example Embodiment

[0023] Example 1

[0024] Method for preparing a lactam compound of the following reaction formula:

[0025]

[0026] Specific steps are as follows:

[0027] 100mL pressure bottle was added to diethylamine (10mmol), benzoic acid (30mmol), sodium hydroxide (30mmol), bromo-sulfonyl fluoride (15mmol), acetonitrile (25mL), at reflux in an oil bath at 50 deg.] C for 18 h, after completion of the reaction, the reaction solution was added 30mL 1M sodium hydroxide solution and then extracted three times with 20mL ethyl acetate, the extract was washed with 20mL 1M hydrochloric acid solution and then dried over anhydrous sodium sulfate and evaporated under reduced pressure, to give the white solid N, N- diethyl-fluoro-benzamide (1.41g, 80% yield).

[0028] Hydrogen spectrum data of this compound obtained in Example amides embodiment is as follows: 1 H-NMH (500MHz, CDCl 3 ) Δ = 7.40-7.36 (m, 5H), 3.56 (s, 2H), 3.26 (s, 2H), 1.26 (s, 3H), 1.11 (s, 3H).

Example Embodiment

[0029] Example 2

[0030] Method for preparing a lactam compound of the following reaction formula:

[0031]

[0032] Specific steps are as follows:

[0033] Was added aniline (10mmol) to a 100mL pressure bottle, o-trifluoromethyl benzoic acid (30mmol), sodium hydroxide (30mmol), bromo-sulfonyl fluoride (15mmol), acetonitrile (25 mL), at 50 deg.] C oil bath under reflux for 18 h, after completion of the reaction, the reaction solution was added 30mL 1M sodium hydroxide solution and then extracted three times with 20mL ethyl acetate. the extract was washed with 20mL 1M hydrochloric acid solution and then dried over anhydrous sodium sulfate Save pressure distillation, to obtain a white solid N- phenyl-2- (trifluoromethyl) benzamide (2.20g, 83% yield).

[0034] Hydrogen spectrum data of this compound obtained in Example amides embodiment is as follows: 1 H-NMH (500MHz, DMSO-d 6 ) Δ = 10.55 (s, 1H), 7.85 (d, J = 7.6Hz, 1H), 7.80 (t, J = 7.3Hz, 1H), 7.73-7.70 (m, 4H), 7.36 (t, J = 7.6 hz, 2H), 7.12 (t, J = 7.3Hz, 1H). 19 F-NMH (500MHz, DMSO-d 6 ), Δ = -57.94 (s, 3F).

Example Embodiment

[0035] Example 3

[0036] Method for preparing a lactam compound of the following reaction formula:

[0037]

[0038] Specific steps are as follows:

[0039] Was added L- valine ethyl ester (10mmol) to a 100mL pressure bottle, benzoic acid (30mmol), sodium hydroxide (30mmol), bromo-sulfonyl fluoride (15mmol), acetonitrile (25 mL), at 50 deg.] C oil after the reaction was refluxed for 18 h at a bath, after completion of the reaction, the reaction solution was added 30mL 1M sodium hydroxide solution and then extracted three times with 20mL ethyl acetate, the extract was washed with 20mL 1M hydrochloric acid solution and then dried over anhydrous sodium sulfate evaporated under reduced pressure to obtain a white solid benzoyl -L- valine ethyl ester (2.17g, 87% yield, 99% ee).

[0040] Hydrogen spectrum data of this compound obtained in Example amides embodiment is as follows: 1 H-NMR (500MHz, CDCL 3 ) Δ = 7.81 (d, J = 7.3Hz, 2H), 7.50 (t, J = 7.3Hz, 1H), 7.44 (t, J = 7.5Hz, 2H), 6.68 (d, J = 7.7Hz, 1H) , 4.76 (dd, J1 = 8.6Hz, J2 = 4.8Hz, 1H), 4.27-4.20 (m, 2H), 2.31-2.25 (m, 1H), 1.30 (t, J = 7.1Hz, 3H), 1.00 ( dd, J1 = 12.4Hz, J2 = 6.9Hz, 6H).

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Classification and recommendation of technical efficacy words

easy to operate
low cost of preparation

Preparation method of amide compound

AI-Extracted Technical Summary

Problems solved by technology

Abstract

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Examples

Example Embodiment

Example Embodiment

Example Embodiment

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Description & Claims & Application Information

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