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2-chloro-N-(phenyl formamyl) nicotinamide compound, preparation method thereof and application of compound

A technology of phenylcarbamoyl and nicotinamides, which is applied in the field of 2-chloro-N-(phenylcarbamoyl) nicotinamides and their preparation and application, and can solve the problem of low atom economy and separation process cumbersome, limited range of reaction substrates, etc.

Inactive Publication Date: 2019-03-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have obvious defects
For example, the use of highly active, expensive and dangerous reagents (such as acid halides, etc.), the reaction produces hydrogen halides, resulting in low atom economy in the amidation reaction, and will corrode equipment and pollute the environment
The subsequent development of enzyme catalysis is also a good method for the synthesis of amides, but there are disadvantages that the activity of the enzyme is affected by the reaction conditions. In addition, the separation process of the enzyme from the reaction system is cumbersome and the scope of the reaction substrate is limited. Applications

Method used

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  • 2-chloro-N-(phenyl formamyl) nicotinamide compound, preparation method thereof and application of compound
  • 2-chloro-N-(phenyl formamyl) nicotinamide compound, preparation method thereof and application of compound
  • 2-chloro-N-(phenyl formamyl) nicotinamide compound, preparation method thereof and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The preparation of 2-chloro-N-(phenylcarbamoyl) nicotinamide compounds, the steps are as follows:

[0032] 1) Add 2-chloronicotinic acid (3.4g, 22mmol) and thionyl chloride (10mL) into a 100mL flask, heat, stir and reflux for 3h until the reaction solution changes from turbid to clear, continue to reflux for 30min, and then react The liquid is subjected to rotary evaporation to remove excess thionyl chloride to obtain a yellow transparent liquid, which turns into a yellow crystal after cooling to room temperature, which is 2-chloronicotinoyl chloride;

[0033] 2) The 2-chloronicotinoyl chloride obtained in step 1) was diluted with 8 mL of dichloromethane, and prepared as a 2-chloronicotinyl chloride solution for later use; under ice bath conditions, the above prepared 2-chloronicotinyl chloride solution was slowly added dropwise to 25% In ammonia water, the dropping rate is 1-2 drops / s. Stir while adding to form a uniform solution. After the dropping is completed, remov...

Embodiment 2

[0038] For the preparation of 2-chloro-N-(phenylcarbamoyl) nicotinamide compounds, the method steps are repeated in Example 1, but the difference from Example 1 is that the same volume of thionyl chloride in step 1) is used Dichloromethane is replaced, and the substituent of the substituted aniline of step 4) is different from that of Example 1, and the final reaction obtains the target product A2;

[0039] Target product A2: white solid, yield: 58.7%, melting point: 181-183°C. 1 H NMR (CDCl 3 ,500MHz), δ:2.33(s,6H,CH 3 ),6.81(s,1H,Ph),7.14(s,2H,Ph),7.42-7.44(m,1H,Py),8.09-8.11(m,1H,Py),8.59-8.60(m,1H, Py),9.46(s,1H,NH),10.38(s,1H,NH); 13 C NMR (CDCl 3 ,150MHz)δ:21.45,117.84,123.45,125.93,131.91,137.70,139.62,137.73,146.49,150.56,151.55,167.78; HRMS (ESI) for C 15 h 14 ClN 3 o 2 m / z: Calculated, 304.0847, Found, 304.0849 [M+H] + .

Embodiment 3

[0041] For the preparation of 2-chloro-N-(phenylcarbamoyl)nicotinamide compounds, the method steps are repeated in Example 1, but the difference from Example 1 is that the amount of thionyl chloride in step 1) is 6mL , the substituent of the substituted aniline in step 4) is different from that of Example 1, and the target product A3 is finally reacted;

[0042] Target product A3: white solid, yield: 65.6%, melting point: 205-208°C. 1 H NMR (CDCl 3 ,500MHz), δ:2.36(s,1H,CH 3 ),7.16(d,J=6.6Hz,2H,Ph),7.38(d,J=6.7Hz,2H,Ph),7.42-7.45(m,1H,Py),8.10-8.12(m,1H,Py ), 8.60-8.62 (m, 1H, Py), 9.39 (s, 1H, NH), 10.37 (s, 1H, NH); HRMS (ESI) for C 14 h 12 ClN 3 o 2 m / z: Calculated, 290.0691, Found, 290.0690 [M+H] + .

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Abstract

The invention discloses a 2-chloro-N-(phenyl formamyl) nicotinamide compound, a preparation method thereof and an application of the compound. The structural formula of the compound is as shown in a formula (I), H on a benzene ring is monosubstituted or polysubstituted by substituent groups R, n is an integer of 1-5 and indicates the number of the substituent groups R on the benzene ring, the H onthe benzene ring is monosubstituted by the substituent groups R when n=1, the H on the benzene ring is polysubstituted by the substituent groups R when n=2-5, the substituent groups R at different substituent positions are the same or different, and the substituent groups R are halogen, C1-C5 alkyl, C1-C5 alkoxy, phenoxy, nitryl, C1-C3 halogenated alkyl, C1-C3 halogenated alkoxy, phenyl or methoxycarbonyl. The compound is a novel compound with bactericidal activity and has a certain inhibiting effect on cucumber botrytis cinerea, sclerotinia sclerotiorum, fusarium graminearum and physalosporapiricola.

Description

technical field [0001] The invention relates to a 2-chloro-N-(phenylcarbamoyl)nicotinamide compound and a preparation method and application thereof. Background technique [0002] Amide fungicides are a kind of common fungicides, which are widely used in crop disease control. There have been a lot of research on the synthesis and biological activity of amide fungicides at home and abroad. Heterocyclic compounds have good selectivity, high activity, and toxicity. Low-level characteristics have become the focus of research and development of agricultural fungicides at home and abroad in recent years. Many compounds containing heterocyclic structures have been used as commercial fungicides and are widely used in the control of crop diseases. [0003] And amides are one of the most common compounds in natural bioactive molecules and synthetic organic compounds. The synthesis of amides has important applications in medicinal chemistry, biochemistry and polymer synthesis. Studie...

Claims

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Application Information

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IPC IPC(8): C07D213/82A01N47/34A01P3/00
CPCA01N47/34C07D213/82
Inventor 刘幸海乔丽汪乔谭成侠翁建全
Owner ZHEJIANG UNIV OF TECH
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