Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
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
View PDF1 Cites 20 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
However, there are still many defects in the above preparation method: expensive catalyst, difficult to obtain, easy to generat
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
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.
[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%.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
PUM
Login to view more
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to view more 
Login to view more