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Preparation method of 4-bromo-N- (pyridine-2-methyl) naphthalene-1-sulfonamide compound

The technology of a compound, bromonaphthalene, is applied in the field of preparation of the compound 4-bromo-N-naphthalene-1-sulfonamide, achieving the effect of simple operation

Active Publication Date: 2010-07-21
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is still no literature report on the synthetic method of 4-bromo-N-(pyridine-2-methyl)naphthalene-1-sulfonamide

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  • Preparation method of 4-bromo-N- (pyridine-2-methyl) naphthalene-1-sulfonamide compound
  • Preparation method of 4-bromo-N- (pyridine-2-methyl) naphthalene-1-sulfonamide compound
  • Preparation method of 4-bromo-N- (pyridine-2-methyl) naphthalene-1-sulfonamide compound

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Embodiment 1

[0021] The synthesis of embodiment 1,4-bromo-N-(pyridine-2-methyl)naphthalene-1-sulfonamide

[0022] 1) Synthesis of potassium 4-bromonaphthalene-1-sulfonate

[0023] Add 41.4g (0.2mol) of 1-bromonaphthalene to a 250mL three-neck round bottom flask, 150mL CCl 4 As a solvent, slowly add 23.3g (0.2mol) of chlorosulfonic acid dropwise in an ice-salt bath at a temperature of 0-5°C. After the drop is complete, stir at room temperature for 12 hours. A large amount of gray solid precipitates. Pour the reaction solution into 200mL of ice water and the solid dissolves. ,Liquid separation. KHCO for aqueous phase 3 Adjust the pH to 7, a large amount of white solids precipitated, filtered and dried to obtain 52.7 g of potassium 4-bromonaphthalene-1-sulfonate with a yield of 81%.

[0024] 2) Synthesis of 4-bromonaphthalene-1-sulfonyl chloride

[0025] Add 32.5 g (0.1 mol) of 4-bromonaphthalene-1-sulfonic acid potassium and 50 mL SOCl to the 100 mL round bottom flask prepared in step 1)...

Embodiment 2

[0033] The synthesis of embodiment 2,4-bromo-N-(pyridine-2-methyl)naphthalene-1-sulfonamide

[0034] The preparation method is basically the same as in Example 1, the difference being that in step 3), a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:3 is used as an eluent for column chromatography to obtain 4-bromo-N-(pyridine -2-Methyl)naphthalene-1-sulfonamide 11.31 g, yield 60%.

[0035] According to hydrogen spectrum and mass spectrum, it is proved that the compound synthesized in this example is consistent with the Pyrabactin structural formula reported in the literature.

Embodiment 3

[0036] The synthesis of embodiment 3,4-bromo-N-(pyridine-2-methyl)naphthalene-1-sulfonamide

[0037] The preparation method is basically the same as in Example 1, the difference being that in step 3), a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:5 is used as an eluent for column chromatography to obtain 4-bromo-N-(pyridine -2-methyl)naphthalene-1-sulfonamide 11.69 g, yield 62%.

[0038] According to hydrogen spectrum and mass spectrum, it is proved that the compound synthesized in this example is consistent with the Pyrabactin structural formula reported in the literature.

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Abstract

The invention discloses a preparation method of a 4-bromo-N-(pyridine-2-methyl) naphthalene-1-sulfonamide compound for inhibiting seed germination, which is disclosed in formula (I). The method comprises the following steps of: using triethylamine as an acid binding agent and reacting 4-bromonaphthalene-1-sulfonyl chloride with 2-aminomethyl pyridine for obtaining the compound shown as formula (I). The method for synthesizing the 4-bromo-N-(pyridine-2-methyl) naphthalene-1-sulfonamide has simple operation; the 4-bromo-N-(pyridine-2-methyl) naphthalene-1-sulfonamide can be synthesized in one step; the yield is higher, which is more than 65%; and the invention provides a method for artificially synthesizing the 4-bromo-N-(pyridine-2-methyl) naphthalene-1-sulfonamide, disclosed in formula (I).

Description

technical field [0001] The invention relates to a preparation method of compound 4-bromo-N-(pyridine-2-methyl)naphthalene-1-sulfonamide for inhibiting seed germination. Background technique [0002] Abscisic acid (ABA) is one of the five major hormones that have been discovered, which can regulate various physiological activities of plants, such as accelerating leaf shedding, inducing dormancy, inhibiting germination and closing stomata, and making changes in the face of adversity stress such as drought and low temperature. response. For example, a kind of plant growth regulating composition (Tan Hong [P].CN 02117265) disclosed by Tan Hong etc. has the function of preventing grain ear bud germination. However, due to the high cost and poor stability of abscisic acid, people have been studying substances with similar activities to abscisic acid. [0003] In 2009, Sang-Youl Park et al. (Sang-Youl Park.Science, 2009, 324, 1068-1071) confirmed that 4-bromo-N-(pyridine-2-methyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/42A01N43/40A01P21/00
Inventor 段留生周繁谭伟明李召虎
Owner CHINA AGRI UNIV
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