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Preparation method of 1H-1,2,3-triazole compound

A 1H-1, compound technology, applied in the direction of organic chemistry, can solve the problems of easy generation of by-products, limited scope of application, expensive catalysts, etc., and achieves the effect of broad industrial application prospects, environmental friendliness and low cost.

Active Publication Date: 2012-07-25
平邑仁安中医药产业发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many defects in the above preparation method: expensive catalyst, difficult to obtain, easy to generate by-products, low yield, limited scope of application, large limitations and harsh conditions, thus limiting its applicability

Method used

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  • Preparation method of 1H-1,2,3-triazole compound
  • Preparation method of 1H-1,2,3-triazole compound
  • Preparation method of 1H-1,2,3-triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the preparation of 1-benzyl-4-phenyl-1,2,3-triazole shown in formula (I-1)

[0027]

[0028] Benzyl bromide (171.0mg, 1mmol) shown in formula (III-1), sodium azide (130mg, 2mmol), phenylacetylene (112.3mg, 1.1mmol) shown in formula (II-1), porous copper (5 μm pore size, 3.2 mg, 0.05 mmol) were mixed in deionized water (4 ml), stirred and reacted in an oil bath at 55° C. for 29 h, followed by TLC. After the reaction, extract with ethyl acetate (10mL×3), wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, column chromatography (petroleum ether:ethyl acetate=5:1), collect R f The eluate with a value of 0.3-0.35 was distilled under reduced pressure and dried to obtain 224.6 mg of the target compound, with a yield of 95.47%, as white needle-like crystals.

[0029] 1 HNMR (CDCl 3 ): δ=7.81-7.83(m, 2H), 7.68(s, 1H), 7.39-7.43(m, 5H), 7.32-7.34(m, 3H), 5.59(s, 2H)

Embodiment 2

[0031] The amount of porous copper was increased to 6.4mg (0.10mmol), the reaction time was 10 hours, other operations were the same as in Example 1, and the yield was 94.9%.

Embodiment 3

[0033] The amount of porous copper was increased to 9.6mg (0.15mmol), the reaction time was 29 hours, other operations were the same as in Example 1, and the yield was 94.81%.

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Abstract

The invention discloses a preparation method of a 1H-1,2,3-triazole compound as shown in a formula (I), which comprises the following steps: mixing halide as shown in a formula (III) with alkyne-terminated compound as shown in a formula (II) and sodium azide, reacting for 5-85 hours at 25-80 DEG C in a reaction solvent under the catalytic action of porous copper; after finishing the reaction, performing after-treatment of the reaction solution to obtain the 1H-1,2,3-triazole compound as shown in the formula (I), wherein the solvent is de-ionized water, acetonitrile, anhydrous ethanol, toluene, acetone, N,N-dimethylformamide, tetrahydrofuran or dioxane. The preparation method provided by the invention adopts one-pot operation, the catalyst can be reused for multiple times, the reaction condition is mild, and the operation is easy and simple.

Description

(1) Technical field [0001] The invention relates to a preparation method of 1H-1,2,3-triazole compound. (2) Background technology [0002] 1H-1,2,3-triazole compounds, as important chemical raw material intermediates, are widely used in the synthesis fields of pesticides and medicines. About the synthetic method of 1H-1,2,3-triazole compounds so far reported less: 1. by polystyrene sulfonyl hydrazide and 1,1-dichloroacetone, obtain α-dichlorocarbonylsulfonyl Hydrazone, and then prepared by cyclization with amine (Makam S. Raghavendra and Yulin Lam, Tetrahedron Letters, 2004, 45, 6129-6132). 2. Preparation via copper-catalyzed 1,3-dipolar cycloaddition (CuACC) click reaction of alkynes / azides (Christian W. Caspar Christensen, and Morten Melda. J. Org. Chem, 2002, 67, 3057-3064). 3. With aniline as raw material, the transfer of diazo group is catalyzed by copper (II), and then under the reduction of sodium ascorbate, the copper (I) obtained catalyzes the 1,3-dipolar cycloa...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D249/04C07D401/04C07D403/06
Inventor 崔冬梅陈颖
Owner 平邑仁安中医药产业发展有限公司
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