Method for preparing acetyl cholesterol-7-one p-toluenesulfonylhydrazone

A technology of p-toluenesulfonylhydrazone and toluenesulfonylhydrazide, which is applied in the field of preparing acetylcholesterol-7-ketone p-toluenesulfonylhydrazone, can solve the problems of product recovery damage, increase, unfavorable total yield, etc., and achieve reduction The effect of overall cost, improvement of preparation yield, and easy recycling

Active Publication Date: 2019-08-20
江西天新药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the post-reaction treatment, the acid catalyst is difficult to recover, and acidic waste liquid is produced, which also causes damage to the recovery of the product in the strongly acidic mother liquor, which is not conducive to the improvement of the total yield

Method used

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  • Method for preparing acetyl cholesterol-7-one p-toluenesulfonylhydrazone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] This example is used to illustrate the method for preparing acetylcholesterol-7-one p-toluenesulfonyl hydrazone provided by the present invention

[0038] Put 50g (about 113mmol) of acetylcholesterol-7-one, 22.5g (about 121mmol) of p-toluenesulfonyl hydrazide, 150g of methanol, and 100g of petroleum ether into the reaction vessel, stir and disperse, and then add 2.5g of strongly acidic cationic resin. After feeding, stir and heat up to 50°C, and keep the temperature at 50±1°C for 4h.

[0039] After the heat preservation is finished, the strongly acidic cationic resin is removed by filtration, and 150 g of the mixed solvent is distilled off from the filtrate under reduced pressure. The remaining feed solution was slowly cooled to 0-5°C, filtered, washed with a small amount of methanol, and vacuum-dried to obtain 66.3 g of acetylcholesterol-7-one p-toluenesulfonylhydrazone, with a content of 98.2%.

Embodiment 2

[0041] This example is used to illustrate the method for preparing acetylcholesterol-7-one p-toluenesulfonyl hydrazone provided by the present invention

[0042] Put 50g (about 113mmol) of acetylcholesterol-7-one, 27.3g (about 147mmol) of p-toluenesulfonyl hydrazide, 250g of methanol, and 250g of petroleum ether into the reaction vessel, stir and disperse, and then add 15g of strong acidic cationic resin. After feeding, keep stirring at 25±1°C for 12 hours.

[0043] After the heat preservation is finished, the strongly acidic cationic resin is removed by filtration, and 400 g of the mixed solvent is distilled off from the filtrate under reduced pressure. Slowly cool the remaining feed solution to 0-5°C, filter, wash with a small amount of methanol, and vacuum-dry to obtain 66.9 g of acetylcholesterol-7-one p-toluenesulfonylhydrazone, with a content of 98.3%.

Embodiment 3

[0045] This example is used to illustrate the method for preparing acetylcholesterol-7-one p-toluenesulfonyl hydrazone provided by the present invention

[0046] Put 50g (about 113mmol) of acetylcholesterol-7-one, 40g (about 215mmol) of p-toluenesulfonyl hydrazide, 250g of ethanol, and 50g of petroleum ether into the reaction vessel, stir and disperse, and then add 10g of strongly acidic cationic resin. After feeding, stir and heat up to 40°C, and keep the temperature at 40±1°C for 4h.

[0047] After the heat preservation is finished, the strongly acidic cationic resin is removed by filtration, and 200 g of the mixed solvent is distilled off from the filtrate under reduced pressure. Slowly cool the remaining feed solution to 0-5°C, filter, wash with a small amount of ethanol, and vacuum-dry to obtain 67.1 g of acetylcholesterol-7-one p-toluenesulfonylhydrazone, with a content of 98.4%.

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Abstract

The invention relates to the field of organic synthesis, and discloses a method for preparing acetyl cholesterol-7-one p-toluenesulfonylhydrazone. The method comprises the following steps: carrying out a contact reaction on acetyl cholesterol-7-one and p-methylbenzenesulfonhydrazide under a condensation reaction condition in a solvent containing cation exchange resin. According to the method for preparing the acetyl cholesterol-7-one p-toluenesulfonylhydrazone, acetyl cholesterol-7-one p-toluenesulfonylhydrazone with a relatively high content can be obtained under mild reaction conditions, sothat the yield of subsequent preparation of 7-dehydrocholesterol is improved. Meanwhile, a catalyst in the method is easy to recycle after the reaction, so that overall cost is reduced.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing acetylcholesterol-7-one p-toluenesulfonyl hydrazone. Background technique [0002] Vitamin D3 is a sterol derivative, also known as niacinamide and cholecalciferol, and is one of the essential vitamins for the human body. Vitamin D3 can improve the body's absorption of calcium and phosphorus, promote growth and bone calcification, so it is often used to treat rickets, osteomalacia and infant tetany; large doses of vitamin D3 can also be used for skin tuberculosis, skin and Treatment of various types of mucous membrane lupus erythematosus. In addition to being used as a medicine, vitamin D3 is also widely used in food and feed additives. [0003] At present, the industrial production method of vitamin D3 is a semichemical synthesis method, and its main raw material is cholesterol extracted from animal brain marrow or lanolin. Firstly, the key intermediate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
CPCC07J41/0005Y02P20/584
Inventor 徐勇智董新电章根宝范卫东
Owner 江西天新药业股份有限公司
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