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Preparation method of N-butyl-5-phenylthiazole-4-formamide derivative

A technology of phenylthiazole and carboxamide, which is applied in the field of preparation of N-butyl-5-phenylthiazole-4-carboxamide derivatives, can solve the problems of difficult preservation, expensive palladium reagent, harsh conditions and the like

Inactive Publication Date: 2014-06-04
CHINA PHARM UNIV
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Problems solved by technology

These methods have all realized the arylation of substituted thiazoles, but the palladium reagent used in the palladium-catalyzed reaction is relatively expensive, and the Pd-catalyzed reaction also has β-H elimination reaction and double bond displacement when the reduction and elimination occurs; while the copper-catalyzed reaction The amount of copper reagent used is large, the organic base reagent is expensive, difficult to store, and the conditions are harsh

Method used

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  • Preparation method of N-butyl-5-phenylthiazole-4-formamide derivative
  • Preparation method of N-butyl-5-phenylthiazole-4-formamide derivative
  • Preparation method of N-butyl-5-phenylthiazole-4-formamide derivative

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Effect test

Embodiment 1

[0017] N-Butyl-2,5-phenylthiazole-4-carboxamide (1)

[0018] Take a reaction tube, add N-butyl-2-phenylthiazole-4-carboxamide (130mg, 0.5mmol) and iodobenzene (153mg, 0.75mmol, 1.5eq), cuprous iodide (19mg, 0.1mmol, 0.2eq), NaOH (40mmg, 1mmol, 2eq), dioxane 2mL, and react in an oil bath at 120°C for 12 hours. The reaction system was cooled to room temperature, diluted with ethyl acetate, and filtered through celite to remove metal residues. The filtrate was washed with water and saturated brine, anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain a dark crude product, which is then subjected to silica gel column chromatography to obtain 155 mg of a white solid with a yield of 92.3%.

[0019] IR: 3046, 3061, 2950, ​​2927, 1669, 1532, 1476, 1224, 769, 718, 689cm-1; 1 H NMR (300MHz, CDCl 3 )δ7.94-7.96(m, 2H), 7.66-7.68(m, 3H), 7.41-7.48(m, 6H), 3.42(q, J=7.0Hz, 2H), 0.95(t, J=7.2Hz ,3H)ppm; 13 C NMR (75MHz, CDCl 3 )δ163.72, 160.55, 142.1, 141.67, 131....

Embodiment 2

[0021] N-Butyl-2-(4-fluorophenyl)-5-phenylthiazole-4-carboxamide (2)

[0022] Take a reaction tube, add N-butyl-2-(4-fluorophenyl)thiazole-4-carboxamide (139mg, 0.5mmol) and iodobenzene (153mg, 0.75mmol, 1.5eq), cuprous iodide ( 19mg, 0.1mmol, 0.2eq), NaOH (40mmg, 1mmol, 2eq), dioxane 2mL, react in 120°C oil bath for 12 hours. The reaction system was cooled to room temperature, diluted with ethyl acetate, and filtered through celite to remove metal residues. The filtrate was washed with water and saturated brine, anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain a dark crude product, which is then subjected to silica gel column chromatography to obtain 150 mg of a white solid with a yield of 85%.

[0023] IR: 3412, 2957, 2873, 1679, 1516, 1474, 1219, 847, 748, 754, 548cm-1; 1 H NMR (300MHz, CDCl 3 )δ7.91-7.96 (m, 2H), 7.64-7.67 (m, 2H), 7.58 (br, 1H), 7.40-7.42 (m, 3H), 7.14-7.19 (m, 2H), 3.41 (q, J=7.0Hz, 2H), 1.56-1.66(m, 2H), 0.95(t, J=7.2Hz, 3H...

Embodiment 3

[0025] N-Butyl-2-(4-chlorophenyl)-5-phenylthiazole-4-carboxamide (3)

[0026] Take a reaction tube, add N-butyl-2-(4-chlorophenyl)thiazole-4-carboxamide (147mg, 0.5mmol) and iodobenzene (153mg, 0.75mmol, 1.5eq), cuprous iodide ( 19mg, 0.1mmol, 0.2eq), NaOH (40mmg, 1mmol, 2eq), dioxane 2mL, react in 120°C oil bath for 12 hours. The reaction system was cooled to room temperature, diluted with ethyl acetate, and filtered through celite to remove metal residues. The filtrate was washed with water and saturated brine, anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain a dark crude product, which is then subjected to silica gel column chromatography to obtain 163 mg of a white solid with a yield of 88%.

[0027] IR: 3268, 2958, 2928, 2871, 1643, 1560, 1500, 1481, 1104, 837, 754, 690cm-1; 1 H NMR (300MHz, CDCl3) δ7.87-7.90(m, 2H), 7.64-7.67(m, 2H), 7.57(br, 1H), 7.40-7.46(m, 5H), 3.41(q, J=6.9 Hz, 2H), 1.56-1.63(m, 2H), 0.95(t, J=7.3Hz, 3H)ppm; 13 C NMR (7...

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Abstract

The invention relates to the field of organic chemistry and in particular relates to a preparation method of an N-butyl-5-phenylthiazole-4-formamide derivative. The N-butyl-5-phenylthiazole-4-formamide derivative is prepared by using thiazole-4-formamide derivative and substituted iodobenzene as a substrate, copper iodide as a catalyst, sodium hydroxide as alkaline and dioxane as a solvent in an oil bath at 120 DEG C. The synthetic method has the advantages of high yield, easily available raw materials, small usage amount of the copper catalyst, no use of expensive organic alkali reagent, simplicity in reaction equipment, high atom economy and the like.

Description

technical field [0001] The invention relates to a preparation method of N-butyl-5-phenylthiazole-4-carboxamide derivatives, belonging to the field of organic chemistry synthesis methodology. Background technique [0002] The thiazole ring structure exists in many natural products and synthetic active substances, and these compounds exhibit important biological activities, such as: antibacterial activity, antiviral activity, antifungal activity, etc. The 5-phenyl substituted thiazole ring not only exists in the drug structure but also exists in many organic functional materials, such as: fluorescent dyes, liquid crystals, etc. The traditional synthesis method of thiazole ring is the Hantzsch synthesis method, which is only suitable for the synthesis of simple thiazole compounds, and the synthesis yield of substituted thiazoles is low. Therefore, transition metal-catalyzed coupling reactions have become an important method for the construction of substituted thiazoles. [00...

Claims

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Application Information

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IPC IPC(8): C07D277/56
CPCC07D277/56
Inventor 姚和权周海嫔徐伟徐进宜吴晓明
Owner CHINA PHARM UNIV
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