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Preparation of alkyl pyridine-2-sulfonic acid amide

A technology of alkylpyridine and sulfonamide, applied in the direction of organic chemistry, etc., can solve problems such as being unsuitable for mass production, complicated reaction process and post-processing process, etc., and achieve the effects of less three wastes, mild reaction conditions, and simple process

Inactive Publication Date: 2009-07-15
阜新奥瑞凯精细化工有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some reactions in this method require a lower temperature (-10°C) (US 5837708), and some reaction processes and post-treatment processes are more complicated (US 6720322), which are not suitable for mass production

Method used

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  • Preparation of alkyl pyridine-2-sulfonic acid amide
  • Preparation of alkyl pyridine-2-sulfonic acid amide

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Embodiment 1

[0013] Embodiment 1: the preparation of 5-picoline-2-sodium sulfonate

[0014] 65g (0.51mol) of sulfurous acid was dissolved in 300mL of water and added to a 500mL reactor, and then 60g of 2-chloro-5-methylpyridine (0.47mol) was added to the reactor. After sealing the kettle, start stirring (rotating speed 160 rev / min), and heat up to 190° C. (pressure reaches 2 MPa). After stirring and reacting for 20 hours, the temperature was lowered to room temperature, and the reaction mixture was taken out, concentrated, and dried to obtain an off-white solid (containing inorganic salt).

Embodiment 2

[0015] Embodiment 2: Preparation of 5-picoline-2-sulfonyl chloride

[0016] Add 112 g of the crude product 5-picoline-2-sulfonate sodium obtained in the previous step, 200 ml of thionyl chloride and 2 ml of N,N-dimethylimine into a 500 mL reaction flask. The reaction mixture was heated to reflux, stirred for 4 hours, and cooled to room temperature. The reaction solution was concentrated to dryness to obtain a reddish-brown oil.

Embodiment 3

[0017] Embodiment 3: the preparation of 5-picoline-2-sulfonamide

[0018] The oil obtained in the previous step was transferred to a 500 mL three-neck reaction flask with 200 mL of dichloromethane, and the reaction flask was cooled in ice water. Slowly add 150 ml of concentrated ammonia water dropwise under stirring, keeping the reaction temperature below 5°C. After the addition was complete (about 0.5 hours), warm to room temperature and continue stirring for 3.0 hours. The organic layer was separated, and the aqueous layer was extracted three times with 300 mL of dichloromethane. The organic layer and the extract were combined, washed with 100 mL of saturated brine, dried over anhydrous sodium sulfate, concentrated to obtain a yellow solid, and recrystallized from petroleum ether to obtain a light yellow solid 60.3 grams, with a purity of 98%. 1 H NMR (D 6 -DMSO, 300 MHz): 2.39 (s, 3H), 7.41 (S, 2H), 7.80-7.88 (m, 2H), 8.55 (S, 1H). LC-MS: t R =1.22min, [M+1] + =173.

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Abstract

The invention relates to a pharmaceutical intermediate, in particular to a method for preparing a key intermediate 5-alkyl-2-pyridine sulfonamide of pyridine sulfonamide miazines pharmaceutical active species. The method has three steps as follows: firstly, 2-alkyl pyridine chloride reacts with sodium sulfite to produce alkyl pyridine-2-sodium sulfonate; secondly, alkyl pyridine-2-sulfonic acid chloride is produced under the effect of chlorinating reagents and finally, pyridine-2-sulfonic acid amide is produced through amination. The method of the invention is simple in technique, mild in reaction conditions, safe and convenient in operation, easy in acquiring the raw materials, high in product yield and purity, few in three wastes and suitable for industrial production.

Description

(1) Technical field [0001] The present invention relates to a kind of preparation method of alkylpyridine-2-sulfonamide (2) Background technology [0002] Alkylpyridine-2-sulfonamides are very important intermediates in pharmaceutical and chemical factories, especially the necessary raw materials for pyridinesulfonamide pyrimidines. [0003] Alkylpyridine-2-ammonia is a very easy-to-get raw material, but because it is difficult to form a stable diazonium salt due to alkylpyridine-2-ammonia, it is usually not used as a raw material for direct synthesis of alkylpyridine-2-sulfonyl chloride (preparation intermediates of alkylpyridine-2-sulfonamides). Literature (such as Acta Poloniae Pharmceutica, 1977, 34 (2) 245-249) reports that at first alkylpyridine-2-ammonia is prepared its hydroxyl product through diazotization reaction, then in P 4 S 10 Under the action, the alkylpyridine-2-mercapto group can be obtained, and finally the alkylpyridine-2-sulfonamide can be obtained by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/71
Inventor 刘春玉金尚德任自跃
Owner 阜新奥瑞凯精细化工有限公司
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