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Sofalcone preparation method

A technology of sofalone and dihydroxyacetophenone, which is applied in the field of preparation of sofalone, can solve the problems of complex process, long reaction steps, low reaction yield and total yield, and achieve shortening of reaction steps and manufacturing cost Reduced effect

Inactive Publication Date: 2006-02-15
阮华君
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The above-mentioned preparation method mainly has the disadvantages of long reaction steps, complicated process, low reaction yield and total yield of each step (the total yield is about 40%), long reaction cycle, etc.

Method used

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Examples

Experimental program
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Embodiment 1

[0029] 1. Add 122 grams (1.00mol) of p-hydroxybenzaldehyde and 152 grams (1.00mol) of 2,4-dihydroxyacetophenone into a 5000mL three-necked bottle, start stirring, add 1500ml of ethanol, cool to 5°C, drop 1150 ml of 20% potassium hydroxide aqueous solution was added, and the stirring reaction was continued for 24 hours. After the reaction was completed, the reactant was poured into ice water, and 16% hydrochloric acid was added dropwise with stirring, neutralized to neutral, continued to stir for 1 hour, filtered, washed with water until neutral, dried, and recrystallized with ethanol to obtain 213 grams of the product, the yield : 83.2%, melting point 201-202.5°C.

[0030] 2. In a 3000ml three-necked bottle, add 210g (0.82mol) 2,4,4-trihydroxychalcone and 1500ml acetone, start stirring, add 340g (2.46mol) potassium carbonate, stir to dissolve all . Start to add 244.4 grams (1.64mol) of bromoisoamylene dropwise, drop it in 20 minutes, start to heat up to reflux, keep the refl...

Embodiment 2

[0033] 1. Add 122 grams (1.00mol) of p-hydroxybenzaldehyde and 136.8 grams (0.90mol) of 2,4-dihydroxyacetophenone into a 5000mL three-necked flask, start stirring, add 1500ml of ethanol, and cool down to -5°C. 1150 ml of 20% potassium hydroxide aqueous solution was added dropwise, and the stirring reaction was continued for 30 hours. After the reaction was completed, the reactant was poured into ice water, and 16% hydrochloric acid was added dropwise with stirring, neutralized to neutral, and stirred for 1 hour, filtered, washed with water until neutral, dried, and recrystallized with ethanol to obtain 207 grams of the product, yield : 80.9%, melting point 201-202.5°C.

[0034] 2. In a 3000ml three-necked bottle, add 210g (0.82mol) 2,4,4-trihydroxychalcone and 1500ml acetone, start stirring, add 340g (2.46mol) potassium carbonate, stir to dissolve all . Start to add 244.4 grams (1.40 mol) of bromoisoamylene dropwise, finish dropping in 20 minutes, start to heat up to 40°C, k...

Embodiment 3

[0037] 1. Add 122 grams (1.00mol) of p-hydroxybenzaldehyde and 197.6 grams (1.30mol) of 2,4-dihydroxyacetophenone into a 5000mL three-necked flask, start stirring, add 1500ml of ethanol, cool to 15°C, drop 1150 milliliters of 20% potassium hydroxide aqueous solution was added, and the stirring reaction was continued for 36 hours. After the reaction was completed, the reactant was poured into ice water, and 16% hydrochloric acid was added dropwise with stirring, neutralized to neutral, and stirred for 1 hour, filtered, washed with water until neutral, dried, and recrystallized with ethanol to obtain 216 grams of the product, the yield : 84.4%, melting point 201-202.5°C.

[0038] 2. In a 3000ml three-necked bottle, add 210g (0.82mol) 2,4,4-trihydroxychalcone and 1500ml acetone, start stirring, add 340g (2.46mol) potassium carbonate, stir to dissolve all . Start to add 308.5 grams (2.07 mol) of bromoisoamylene dropwise, finish dropping in 20 minutes, stir and react at room temp...

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Abstract

Disclosed is a Sofalcone preparation method which mainly comprises, (1) subjecting p-hydroxybenzaldehyde and 2,4-ihydroxyacetophenone to condensation reaction under alkaline condition, obtaining 2,4,4-Trihydro-xychalcone, (2) subjecting 2,4,4-trihydro-xychalcone and 1-bromo-3-methyl-2-butene to condensation reaction, obtaining 2-hydroxyl-4,4-bis (3-methyl-2-butenyloxy) chalcone, (3) subjecting the 2-hydroxyl-4,4-bis (3-methyl-2-butenyloxy) chalcone and ethyl bromoacetate to condensation under the action of potasium carbonate, thus obtaining sofalcone. The mol ratio of p-hydroxybenzaldehyde, 2.4-dihydroxyacetophenone, 1-bromo-3-methyl-2-butene, and ethyl bromoacetate can be 1 : (0.90-1.50) : (1.60-2.55) : (0.60-1.25).

Description

technical field [0001] The invention relates to a preparation method of sofalone, which belongs to the technical field of chemical pharmacy. Background technique [0002] Sofadone is a highly effective drug for the treatment of chronic gastritis, gastric ulcer and duodenal ulcer. It expands gastric mucosal blood vessels, increases gastric mucosal blood flow and gastric tissue oxygen consumption, and promotes gastric mucosal repair; Inhibits prostaglandin-decomposing enzymes, thereby increasing the content of prostaglandins in the stomach and playing an anti-gastric ulcer effect. [0003] According to the reports of U.S. patents and literature, sofalone is prepared through the following four-step reactions: [0004] 1. 4-(3-methyl-2-butenyloxy)-2-hydroxyacetophenone is generated by condensation of 2,4-dihydroxyacetophenone and bromoisoamylene under alkaline conditions. [0005] 2, 4-(3-methyl-2-butenyloxy)-2-hydroxyacetophenone is condensed with ethyl br...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/215C07C51/00C07C51/295
Inventor 阮华君
Owner 阮华君
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