Method for preparing amide compound

A technology of amide compounds and substances, which is applied in the field of preparation of amide compounds, can solve the problems of high price, limited large-scale application, and cumbersome catalytic system, and achieves the effects of mild reaction conditions, high compatibility, and reduced pollution

Inactive Publication Date: 2012-10-24
云梦星联物流有限公司
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many methods for synthesizing amides, some of these methods use expensive catalysts (such as Ru, Rh, Pd, Ni, Cu), some catalytic systems are more complicated, some reactants are troublesome to prepare, and the price is relatively expensive. The scope of use is narrow and has relatively large limitations, which limit its large-scale application

Method used

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  • Method for preparing amide compound
  • Method for preparing amide compound
  • Method for preparing amide compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Add I to the reaction flask sequentially under the reaction condition of zero degrees Celsius 2 (1.5 mmol), compound a 1 (2 mmol), compound b 1 (2 mmol), solvent isopropanol 2mL, after stirring for 5 minutes, the oxidant TBHP (6 mmol) was added. Then the system was stirred for about 12 hours at zero degrees Celsius in the air, then quenched by adding saturated sodium thiosulfate solution, extracted with ethyl acetate (2 mL×3), then adsorbed with 100-200 mesh silica gel, and passed through 300-400 mesh silica gel column eluting to obtain the product c 11 , the yield is 90%. 1 H NMR (CDCl 3 , 400 MHz): δ 7.78 – 7.76 (m, 2H), 7.48 – 7.44 (m, 1H), 7.40 – 7.37 (m, 2H), 6.62 (s, 1H), 3.44 – 3.39 (m, 2H), 1.61 – 1.54 (m, 2H), 1.43 – 1.33 (m, 2H), 0.93 (t, J = 7.4 Hz, 3H); 13 C NMR (CDCl 3 , 100 MHz): δ 167.5, 134.7, 131.1, 128.3, 126.8, 39.7, 31.6, 20.1, 13.6; MS (ESI) m / z [M+H] + Calcd for C 11 h 16 NO: 178, found: 178; IR (KBr, cm -1 ): ν 1641. Th...

Embodiment 2

[0029]

[0030] Add (CH 3 ) 4 NI (1.2 mmol), compound a 2 (1 mmol), compound b 1 (2 mmol), solvent dichloromethane 2mL, after stirring for 5 minutes, the oxidant TBHP (6 mmol) was added. After stirring for about 12 hours at zero degrees Celsius in the air, add saturated sodium thiosulfate solution to quench the reaction, extract with ethyl acetate (2 mL×3), then absorb with 100-200 mesh silica gel, and pass through 300-400 The product c was obtained by eluting with a silica gel column 21 , and the yield was 82%. 1 H NMR (CDCl 3 , 300 MHz): δ 7.64 (d, J = 8.2 Hz, 2H), 7.49 (d, J = 8.2 Hz, 2H), 6.88 (s, 3H), 3.42 – 3.35 (m, 2H), 1.56 – 1.51 (m, 2H), 1.37 – 1.32 (m, 2H), 0.92 (t, J = 7.2 Hz, 2H); 13 C NMR (CDCl 3 , 75 MHz): δ 166.7, 133.5, 131.5, 128.5, 125.7, 39.8, 31.5, 20.0, 13.7; MS (ESI) m / z [M+H] + Calcd for C 11 h 15 79 BrNO: 256, found: 256; C 11 h 15 81 BrNO: 258, found: 258; IR (KBr, cm -1 ): ν 1635. The above detection data confirmed that the...

Embodiment 3

[0032]

[0033] Add (CH 3 ) 3 PhCH 2 N 4 I (1.5 mmol), compound a 3 (3 mmol), compound b 1 (4 mmol), solvent 1,1,1-trichloroethane 2mL, after stirring for 5 minutes, the oxidant TBHP (7 mmol) was added. Then the system was stirred for about 12 hours at zero degrees Celsius in the air, then quenched by adding saturated sodium thiosulfate solution, extracted with ethyl acetate (2 mL×3), then adsorbed with 100-200 mesh silica gel, and passed through 300-400 mesh silica gel column eluting to obtain the product c 31 , and the yield was 83%. 1 H NMR (CDCl 3 , 300 MHz): δ7.71 (d, J = 8.5 Hz, 2H), 7.33 (d, J = 8.5 Hz, 2H), 6.89 (s, 1H), 3.42 – 3.36 (m, 2H), 1.57 – 1.52 (m, 2H), 1.37 – 1.32 (m, 2H), 0.92 (t, J = 7.2 Hz, 2H); 13 C NMR (CDCl 3 , 75 MHz): δ166.6, 137.3, 133.1, 128.5, 128.3, 39.8, 31.5, 20.0, 13.6; MS (ESI) m / z [M+H] + Calcd for C 11 h 15 35 ClNO: 212, found: 212; C 11 h 15 37 ClNO: 214, found: 214; IR (KBr, cm -1 ): ν 1630. The above detection d...

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Abstract

The invention discloses a method for preparing an amide compound, which comprises the steps of configuration of reaction system. Methyl ketone, amine, catalyst, an oxidizing agent and solvent are use, wherein the general formula of the methyl ketone is RCOCH3, and R is selected from one kind of C6-C14 aryl group, C2-C8 alkenyl group, and five-or six-membered heterocyclic group; the amine is primary amine; the catalyst is selected from one kind of potassium iodide, iodine, tetramethyl ammonium iodide, tetrabutyl ammonium iodide, tetrahexyl ammonium iodide, bismuth iodide, lithium iodide, phenyl trimethyl ammonium iodide, benzyl trimethyl ammonium iodide or sodium iodide; the oxidizing agent is tert-butyl hydroperoxide; the solvent is selected from one kind of water, dichloromethane, ethyl acetate, toluene, 1,2-dichloroethane, 1,1,1-trichloroethane, acetonitrile, and isopropanol. The methyl ketone, the catalyst and the amine are added into the reaction system under the temperature of 0 DEG C and stirred for 5 minutes, and then the oxidizing agent is added to react for 2-48 hours to obtain the amide compound. The method provided by the invention is green, moderate, high in selectivity and wide in application range.

Description

technical field [0001] The present invention relates to a method for preparing amide compounds, in particular to a novel method of using iodine-containing compounds as catalysts to catalyze the oxidation of the carbonyl on methyl ketone under the action of tert-butyl hydroperoxide and couple with amines to obtain amide compounds method. Background technique [0002] Amide compounds are a very important class of organic compounds, which can be used not only as structural units of physiologically active natural products, but also widely used in the synthesis of some pharmaceutical intermediates. [0003] At present, the preparation methods of amide compounds mainly contain the following types: [0004] The amide compound is synthesized by carboxylic acid derivatives and amines. The main disadvantage of this synthesis method is that the sources of carboxylic acid derivatives are not extensive and a large amount of alkali is used. J.M.J.Williams et al reported the use of carbo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/06C07C231/14C07C233/65C07D333/38C07C235/46C07D307/68C07D213/81C07C303/30C07C309/73C07C233/69C07C233/73
Inventor 万小兵魏伟陈继君
Owner 云梦星联物流有限公司
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