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Preparation method of olsalazine disodium and postprocessing method of methyl sulfonation reaction

A technology for chemical reaction of olsalazine sodium, applied in the field of preparation of olsalazine sodium, can solve the problems of high product impurities, complicated operation and high cost, and achieve the effects of less product impurities, ensuring product quality and improving yield

Active Publication Date: 2014-02-19
浙江华润三九众益制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the defects that organic solvents such as chloroform and toluene need to be used in the mesylation reaction step in the preparation of olsalazine sodium in the prior art, which have high toxicity, cumbersome operation and high cost, or The method of using whole crushed ice also has the defect that the final product obtained has more impurities. A preparation method of olsalazine sodium and a post-treatment method of mesylation reaction are provided. The method is simple and non-toxic, and the product impurities are obtained. less, the yield is greater than 85%, and the effect is remarkable

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Nitrification reaction, esterification reaction, reduction reaction, diazotization coupling reaction and hydrolysis reaction in the preparation process of olsalazine sodium are with reference to " the improvement of olsalazine synthesis technique " (Chen Xiaoquan, Zhai Hu etc., Chinese pharmacy, 2008, 19 (16): 1222-1223), "Synthetic Improvement of Osalazine" (Du Haitang, Contemporary Chemical Industry, 2006, 35(3): 161-162), "Experimental Research on the Synthesis of Osalazine" (Zhang Wei, Dong Yuefen et al., Hebei Chemical Industry, 2007, 30(12): 47-48).

[0022] Mesylation reaction: put 200 parts (parts by weight) of 5-nitrosalicylic acid methyl ester and 130 parts of pyridine into the reaction kettle, heat the temperature to 38 ° C ~ 42 ° C, the solids are completely dissolved, and add Stir while adding 150 parts of methanesulfonyl chloride until the addition is complete; continue to heat up to 58°C to 62°C, and keep the temperature for 1 hour. Add 48 parts of ice-w...

Embodiment 2

[0024] Nitrification reaction, esterification reaction, reduction reaction, diazotization coupling reaction and hydrolysis reaction in the preparation process of olsalazine sodium are with reference to " the improvement of olsalazine synthesis technique " (Chen Xiaoquan, Zhai Hu etc., Chinese pharmacy, 2008, 19 (16): 1222-1223), "Synthetic Improvement of Osalazine" (Du Haitang, Contemporary Chemical Industry, 2006, 35(3): 161-162), "Experimental Research on the Synthesis of Osalazine" (Zhang Wei, Dong Yuefen et al., Hebei Chemical Industry, 2007, 30(12): 47-48).

[0025] Mesylation reaction: put 200 parts (parts by weight) of 5-nitrosalicylic acid methyl ester and 130 parts of pyridine into the reaction kettle, heat the temperature to 38 ° C ~ 42 ° C, the solids are completely dissolved, and add 150 parts of methanesulfonyl chloride were stirred while adding until the addition was complete. Continue to heat up to 58°C-62°C and keep warm for 1 hour. Add 2400 parts of ice-wate...

Embodiment 3

[0027] Nitrification reaction, esterification reaction, reduction reaction, diazotization coupling reaction and hydrolysis reaction in the preparation process of olsalazine sodium are with reference to " the improvement of olsalazine synthesis technique " (Chen Xiaoquan, Zhai Hu etc., Chinese pharmacy, 2008, 19 (16): 1222-1223), "Synthetic Improvement of Osalazine" (Du Haitang, Contemporary Chemical Industry, 2006, 35(3): 161-162), "Experimental Research on the Synthesis of Osalazine" (Zhang Wei, Dong Yuefen et al., Hebei Chemical Industry, 2007, 30(12): 47-48).

[0028] Mesylation reaction: put 200 parts (parts by weight) of 5-nitrosalicylic acid methyl ester and 130 parts of pyridine into the reaction kettle, heat the temperature to 38 ° C ~ 42 ° C, the solids are completely dissolved, and add 150 parts of methanesulfonyl chloride were stirred while adding until the addition was complete. Continue to heat up to 58°C-62°C and keep warm for 1 hour. Add 240 parts of ice-water...

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Abstract

The invention relates to a preparation method of olsalazine disodium and a postprocessing method of methyl sulfonation reaction. The preparation method uses salicylic acid as a raw material, and the olsalazine disodium is prepared by nitratlon reaction, esterification reaction, the methyl sulfonation reaction, reduction reaction, diazotization coupling reaction and hydrolysis reaction, ice water mixture is added in reaction liquid after the methyl sulfonation reaction in a methyl stlfonation reaction process is completed to process and collect 2-methyl sulfonyl oxygen-5-nitryl methyl benzoate, and the mass ratio of ice to water in the ice water mixture is 0.1:1-10:1. The postprocessing method of the methyl sulfonation reaction is that the ice water mixture is added in the reaction liquid after the methyl sulfonation reaction is completed to process and collect products, and the mass ratio of ice to water in the ice water mixture is 0.1:1-10:1. The method is simple and non-toxic, prepared products are few in impurities, the productivity is higher than 85%, and effects are obvious.

Description

technical field [0001] The invention relates to a preparation method of olsalazine sodium and a post-treatment method of mesylation reaction. technical background [0002] Osalazine sodium is prepared from salicylic acid through nitration, esterification, mesylation, reduction, diazotization coupling, and hydrolysis. According to open documents: "Improvement of Osalazine Synthetic Process" (Chen Xiaoquan, Zhai Hu, etc., Chinese Pharmacy, 2008, 19 (16): 1222-1223), "Synthetic Improvement of Osalazine" (Du Haitang, Modern Chemical Industry, 2006, 35(3): 161-162), "Experimental Research on the Synthesis of Osalazine" (Zhang Wei, Dong Yuefen, etc., Hebei Chemical Industry, 2007, 30(12): 47-48), etc. The preparation of olsalazine sodium involves the step of mesylation reaction, which is treated with hydrochloric acid and then extracted with organic solvents such as chloroform. This method has high toxicity, cumbersome operation and high cost. [0003] For the step reaction of m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C245/08C07C309/66C07C303/44
Inventor 周益成朱菊红王小松金鑫
Owner 浙江华润三九众益制药有限公司