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Preparation method of alpha-keto amide

A technology of ketoamide and primary amine, which is applied in the field of preparation of α-ketoamide, which can solve the problems of cumbersome steps and achieve the effects of reduced pollution, excellent yield and short preparation cycle

Inactive Publication Date: 2014-05-14
南通亚龙消防器材有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(2) After multi-step conversion preparation, this type of method generally has cumbersome steps and requires some special substrates

Method used

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  • Preparation method of alpha-keto amide
  • Preparation method of alpha-keto amide
  • Preparation method of alpha-keto amide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A kind of preparation method of α-ketoamide, its reaction formula is as follows:

[0033]

[0034] The reaction bottle is filled with I 2 (1mmol), compound a 1 (2mmol), compound b 1 (2mmol), the solvent isopropanol 2mL. Then the system was stirred in air at room temperature for about 12 hours, then quenched by adding saturated sodium thiosulfate solution, extracted with ethyl acetate (2mL×3), then adsorbed with 100-200 mesh silica gel, and passed through 300- 400 mesh silica gel column eluting to obtain product c 11 , the yield was 90%. 1 H NMR (CDCl 3 , 400MHz): δ7.98-7.95(m, 2H), 7.68-7.64(m, 1H), 7.55-7.51(m, 2H), 3.81(t, J=4.0Hz, 2H), 3.79(t, J =4.0Hz, 2H), 3.66(t, J=4.0Hz, 2H), 3.39(t, J=4.0Hz, 2H); 13 C NMR (CDCl 3 , 100MHz): δ191.0, 165.2, 134.8, 132.8, 129.4, 128.9, 66.5, 66.4, 46.0, 41.4.; HRMS (ESI) m / z [M+H] + Calcd for C 12 h 14 NO 3 : 220.0968, found: 220.0975; IR(KBr, cm -1 ): v1681, 1645. The above detection data confirmed that the target...

Embodiment 2

[0036] A kind of preparation method of α-ketoamide, its reaction formula is as follows:

[0037]

[0038] The reaction flask was filled in sequence (CH 3 ) 4 NI (0.5mmol), compound a 2 (1 mmol), compound b 1 (2mmol), solvent dichloromethane 2mL. After stirring at room temperature in air for about 12 hours, the reaction was quenched by adding saturated sodium thiosulfate solution, extracted with ethyl acetate (2mL×3), then adsorbed with 100-200 mesh silica gel, and then passed through 300-400 mesh silica gel The product c was obtained by column elution 21 , the yield was 82%. 1 H NMR (CDCl 3 , 400MHz): δ7.83(d, J=8.6Hz, 2H), 7.68(d, J=8.6Hz, 2H), 3.79(t, J=4.0Hz, 4H), 3.67(t, J=4.0Hz , 2H), 3.38(t, J=4.0Hz, 2H); 13 C NMR (CDCl 3 , 75MHz): δ189.8, 164.7, 132.3, 131.7, 130.9, 130.3, 66.5, 66.4, 46.1, 41.5; HRMS (EI) m / z [M] + Calcd for C 12 h 12 79 BrNO 3 : 297.0001, found: 297.0007; Calcd for C 12 h 12 81 BrNO 3 : 298.9980, found: 299.0022; IR(KBr, cm -1): ...

Embodiment 3

[0040] A kind of preparation method of α-ketoamide, its reaction formula is as follows:

[0041]

[0042] The reaction flask was filled in sequence (CH 3 ) 3 PhCH 2 N 4 I (0.5mmol), compound a 3 (3mmol), compound b 1 (4mmol), solvent 1,1,1-trichloroethane 2mL. Then the system was stirred in air at room temperature for about 12 hours, then quenched by adding saturated sodium thiosulfate solution, extracted with ethyl acetate (2mL×3), then adsorbed with 100-200 mesh silica gel, and passed through 300- 400 mesh silica gel column eluting to obtain product c 31 , the yield was 83%. 1 H NMR (CDCl 3 , 400MHz): δ9.25(d, J=8.7Hz, 1H), 8.14(d, J=8.2Hz, 1H), 8.05-8.03(m, 1H), 7.93(d, J=8.1Hz, 1H) , 7.73-7.69(m, 1H), 7.63-7.55(m, 2H), 3.88-3.78(m, 4H), 3.67(t, J=4.0Hz, 2H), 3.44(t, J=4.0Hz, 2H ); 13 C NMR (CDCl 3 , 75MHz): δ193.4, 165.8, 136.0, 134.3, 133.8, 130.6, 129.3, 128.6, 128.1, 126.9, 125.5, 124.3, 66.41, 66.40, 46.1, 41.5; HRMS (ESI) m / z [M+H] + Calcd for C 16 h ...

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Abstract

The invention discloses a preparation method of alpha-keto amide, which comprises the following steps: (a), preparing a reaction system comprising methyl ketone, amine compounds, a catalysts, an oxidant and a solvent, wherein the general formula of methyl ketone is RCOCH3, and R is selected from one of C6-C14 of aryl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy or alkyl sulphanyl, C2-C8 phenolic group as a protection group, unsubstituted five-member or six-member heterocyclic group and substituted five-member or six-member heterocyclic group, and the amine compounds are selected from primary amine or secondary amine; and (b), mixing the reaction system to react for 2-48 hours at a room temperature to obtain alpha-keto amide. The invention discloses a new preparation method of alpha-keto amide. The reaction condition is moderate, and the reaction can undergo under the air condition without a complicated operation procedure; in addition, the preparation method is environment-friendly and meets the requirement and the direction of the contemporary green chemistry development.

Description

technical field [0001] The invention relates to a preparation method of α-ketoamide, which belongs to the field of organic synthesis. Background technique [0002] α-Ketoamide 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 method of α-ketoamide compound mainly contains following several kinds: (1) halogenated benzene, carbon monoxide and secondary amine synthesize α-ketoamide compound under palladium catalysis, the shortcoming of this method mainly needs to use noble metal catalyst, Moreover, carbon monoxide gas under high pressure will be used, the reaction conditions are harsh, and the operation is complicated. See literature (Ozawa, F.; Soyama, H.; Yamamoto, T.; Yamamoto, A. Tetrahedron Lett. 1982, 23, 3383. or F. Ozawa, H.; Soyama, H.; Yanagihara, I.; Aoyam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/10C07C235/80C07D295/12C07D211/46C07D211/62C07D213/40C07D213/74C07D217/06C07D241/12C07D277/28C07D307/81C07D333/22C07D333/28
CPCY02P20/55
Inventor 万小兵魏伟司马文华张凤张超
Owner 南通亚龙消防器材有限公司
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