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Synthesis method of apronal

A technology of valproic acid urea and synthesis method, which is applied in chemical instruments and methods, preparation of urea derivatives, preparation of organic compounds, etc., can solve the problems of using many kinds of raw materials, consuming more energy, increasing costs, etc., and achieve the synthesis route Simple and efficient, low cost and high raw material utilization

Inactive Publication Date: 2017-12-22
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] This route needs 3 steps to obtain the target product, the yield of the first step is only 43%, and the yield is low; and in the first step, it needs to be refluxed for more than 30 hours, consumes a lot of energy, takes a long time, and uses many types of raw materials, including allyl Bromide, 2-bromopropane, etc., resulting in an increase in cost

Method used

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  • Synthesis method of apronal
  • Synthesis method of apronal
  • Synthesis method of apronal

Examples

Experimental program
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Effect test

Embodiment 1

[0028]

[0029] 1. Synthesis of 2-isopropyl-4-enpentanoic acid

[0030] Add 15 mL of tetrahydrofuran and 10 mL of 2.0 mol / L lithium diisopropylamide in tetrahydrofuran to a 100 mL Reyk bottle, and then add 1.1 mL (10.0 mmol) of isovaleric acid represented by formula A-1 dropwise at -15°C, React for 1 hour, then add 1.04mL (12.0mmol) allyl bromide, return to room temperature naturally, continue the reaction for 1 hour, adjust the pH value to 1-2 with 10% hydrochloric acid, add 20mL petroleum ether for extraction, and then Wash with 15 mL of 10% hydrochloric acid, water and brine, combine the organic phases, add anhydrous sodium sulfate to dry, and remove the organic solvent under reduced pressure to obtain 1.2 g of 2-isopropyl-4-enpentanoic acid represented by formula D , the yield is 86%, and the structural characterization data are as follows: 1 H NMR (600MHz, CDCl 3 )δ5.71(td,J 1 =17.0,6.9Hz,1H),4.98(dd,J 1 =38.7,J 2 =13.6Hz, 2H), 2.32-2.22(m, 2H), 2.20-2.13(m, 1H), ...

Embodiment 2

[0034]

[0035] 1. Synthesis of 2-isopropyl-4-enpentanoic acid

[0036]Dissolve 0.9g (7.7mmol) of potassium tert-butoxide in 15mL of tetrahydrofuran, stir at -78°C for 20 minutes, then add 1.2mL (7.7mmol) of ethyl isovalerate represented by formula A-2 dropwise into the reaction system , reacted at -78°C for 2.5 hours, then added 0.6mL (8.1mmol) of allyl bromide represented by formula B dropwise into the reaction system, continued to react at -78°C for 2.5 hours, and removed the organic solvent under reduced pressure to obtain Add 20 mL of ethanol and 55 mL of 3mol / L NaOH aqueous solution to the 2-isopropyl-4-valerate ethyl ester shown in formula C-2, react at 55°C for 12 hours, pour the reaction solution into 30 mL of 10% glacial hydrochloric acid, then extracted twice with 50mL of petroleum ether, combined the organic phases, and washed them with 15mL of 10% hydrochloric acid, water and brine respectively, combined the organic phases, added anhydrous sodium sulfate to dry...

Embodiment 3

[0040] Potassium tert-butoxide in Step 1 of Example 2 is replaced by equimolar lithium diisopropylamide, other steps are the same as in Example 2, the yield of 2-isopropyl-4-valerate is 80%, and the rest The steps and yields are the same.

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Abstract

The invention discloses a synthesis method of apronal. The synthesis method takes isopentanoic acid or isopentanoate which is commercially cheap and available as a synthesis raw material and comprises the following steps: enabling the synthesis raw material and allyl bromide to react under an alkaline condition to generate 2-isopropyl-4-pentenoic acid or 2-isopropyl-4-pentanoate; hydrolyzing the 2-isopropyl-4-pentanoate under the alkaline condition to generate the 2-isopropyl-4-pentenoic acid; then transforming the 2-isopropyl-4-pentenoic acid into acyl chloride and enabling the acyl chloride to react with urea to obtain the apronal. According to the synthesis method disclosed by the invention, a synthesis route can realize medium-scale preparation of the apronal, with the need of two-step or three-step chemical transformation; the whole synthesis route is simple and efficient, simple and convenient to operate, low in cost and high in yield so that the synthesis method is suitable for large-quantity synthesis of the apronal.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of valproic acid urea. Background technique [0002] Valproylurea is a hypnotic / sedative drug. In 1926, the compound was synthesized by Hoffman-Roche Company and is known to the world under the trade name of "Sizionide". At the same time, valproic acid urea is also used as a general drug buffer, and is widely used clinically as a hypnotic drug. [0003] In 1948, valproic acid urea was named "propylallyl acetylurea" in "Japanese Quasi-Pharmacopoeia" (third revision). In 2003, the SG compound granules with antipyretic and pain-relieving effects launched by Shionogi Pharmaceutical Company of Japan contain this ingredient. In general medical drugs, valproic acid is also widely used, for example, its use in EVE Quick is very popular. EVE Quick is added with "ibuprofen" which has the ingredients of suppressing headaches, together with the ad...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C273/18C07C275/50
Inventor 赵玉明刘文杰王超
Owner SHAANXI NORMAL UNIV
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