Method for synthesizing amide

A synthetic method and amide technology, applied in the formation/introduction of amide groups, carboxylic acid amide preparation, chemical instruments and methods, etc., to achieve the effect of broad development prospects

Inactive Publication Date: 2017-10-10
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the reaction to prepare amides catalyzed by these currently known transition metal catalysts uses large amounts of strong inorganic bases, especially KOH

Method used

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  • Method for synthesizing amide
  • Method for synthesizing amide
  • Method for synthesizing amide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: N-benzyl-4-hydroxybutyramide

[0026] N‐benzyl‐4‐hydroxybutanamide

[0027]

[0028] 1,4-Butanediol (91 mg, 1 mmol), cat.[Ir] (5.4 mg, 0.01 mmol, 1 mol%) and tert-amyl alcohol (1 ml) were sequentially added into a 5 mL round bottom flask. After the reaction mixture was refluxed in air for 6 hours, benzylamine (118 mg, 1.1 mmol) was added, and the reaction was continued for 12 hours, then cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 90%

[0029] 1 H NMR (500MHz, CDCl 3 )δ7.36‐7.27 (m, 5H), 5.94 (br, 1H), 4.44 (d, J = 5.7Hz, 2H), 3.71 (t, J = 5.8Hz, 2H), 2.39 (t, J = 6.6 Hz,2H),1.91(q,2H); 13 C NMR (125MHz, CDCl 3 )δ173.5, 138.0, 128.6, 127.6, 127.4, 61.9, 43.5, 33.6, 28.1.

Embodiment 2

[0030] Example 2: N-(4-methylbenzyl)-4-hydroxybutanamide

[0031] N‐(4‐methylbenzyl)‐4‐hydroxybutanamide

[0032]

[0033] 1,4-Butanediol (91 mg, 1 mmol), cat.[Ir] (5.4 mg, 0.01 mmol, 1 mol%) and tert-amyl alcohol (1 ml) were sequentially added into a 5 mL round bottom flask. After the reaction mixture was refluxed in air for 6 hours, 4-methylbenzylamine (133 mg, 1.1 mmol) was added, and the reaction was continued for 12 hours, then cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 88%

[0034] 1 H NMR (500MHz, CDCl 3 )δ7.17‐7.13 (m, 4H), 5.97 (br, 1H), 4.39 (d, J = 5.7Hz, 2H), 3.69 (t, J = 5.8Hz, 2H), 2.37 (t, J = 6.7 Hz,2H),2.33(s,3H),1.89(q,2H); 13 C NMR (125MHz, CDCl 3 )δ173.5, 137.0, 135.0, 129.2, 127.6, 61.8, 43.2, 33.5, 28.1, 20.9.

Embodiment 3

[0035] Example 3: N-(3-methylbenzyl)-4-hydroxybutanamide

[0036] N‐(3‐methylbenzyl)‐4‐hydroxybutanamide

[0037]

[0038] 1,4-Butanediol (91 mg, 1 mmol), cat.[Ir] (5.4 mg, 0.01 mmol, 1 mol%) and tert-amyl alcohol (1 ml) were sequentially added into a 5 mL round bottom flask. After the reaction mixture was refluxed in air for 6 hours, 3-methylbenzylamine (133 mg, 1.1 mmol) was added, and the reaction was continued for 12 hours, then cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 82%

[0039] 1 H NMR (500MHz, CDCl 3 )δ7.22‐7.19 (t, J=7.57Hz, 1H), 7.09‐7.04 (m, 3H), 6.15 (br, 1H), 4.37 (d, J=5.4Hz, 2H), 3.67 (t, J =5.9Hz, 2H), 2.37(t, J=6.6Hz, 2H), 2.33(s, 3H), 1.89(q, 2H); 13 C NMR (125MHz, CDCl 3 )δ173.3, 138.4, 137.9, 128.6, 128.5, 128.2, 124.7, 62.1, 43.6, 33.7, 28.1, 21.3.

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Abstract

The invention discloses a method for synthesizing amide. The method includes the steps: adding dihydric alcohol, Iridium complex catalysts and solvent tert-amyl alcohol into a reaction vessel; performing reflux reaction on reaction mixture in oil bath, and adding compound amine several hours after; continuing to react for several hours, and cooling reaction mixture to reach indoor temperature; performing rotary evaporation to remove solvents, and performing column separation to obtain a target compound. The method adopts bi-functional catalysts of ligands with dipyridyl, the dihydric alcohol serves as a raw material, the catalysts and the dihydric alcohol directly react in air for 18 hours to obtain the target compound, alkaline environments are omitted, obvious advantages are shown, requirements of green chemistry are met, and the method has a wide development prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a synthesis method of amides. Background technique [0002] The formation of amide bonds is an important reaction in organic synthetic chemistry and biology. Amide compounds, as an important class of compounds, exhibit a wide range of physiological and pharmacological activities. Such compounds can be used as important drug intermediates to synthesize biologically active small molecules and prepare antispasmodic agents and the like. (a) R.Z.Fu, Y.Yang, Y.S.Ma, F.Yang, J.J.Li, W.Chai, Q.Wang, R.G.Yuan. Tetrahedron Lett. 2015, 56, 4527–4531; b) R.S.Coronado, R.C.Peralta, S.S.Ruiz, R. Contreras, A.F. Parr. J. Organomet. Chem. 2009, 694, 616‐622; c) M.A. Glomb, C. Pfahler, JBC Papers. 2001, 276, 41638‐41647.) [0003] The traditional method of synthesizing amide compounds is to react carboxylic acid derivatives with amines, which has high reaction te...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/10C07C235/06C07C235/08C07C237/06C07C235/46C07D307/52C07D333/20C07B43/06
CPCC07B43/06C07C231/10C07D307/52C07D333/20C07C235/06C07C235/08C07C237/06C07C235/46
Inventor 徐梦李顺李峰
Owner NANJING UNIV OF SCI & TECH
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