Preparation method of alpha-keto amide
The technology of ketone amide and methyl ketone is applied in the field of preparation of α-keto amide, which can solve the problems of cumbersome steps and the like, and achieve the effects of reducing pollution, high compatibility and environmental friendliness.
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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 the 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 ta...
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), the solvent dichloromethane 2mL. After stirring at room temperature in air for about 12 hours, add saturated sodium thiosulfate solution to quench the reaction, extract with ethyl acetate (2mL×3), then absorb with 100-200 mesh silica gel, and pass 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): v 1676, 1628. T...
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 the 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 1...
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