Method for preparing compound of 1, 2 (dodecyl) 4 hydroxide methylene - 3, 5 pyrazole

A technology of pyrazolidinedione and hydroxymethylene, which is applied in 1 field, can solve problems such as the synthesis of undisclosed compounds, and achieve the effects of simple post-processing, high product purity, and advanced synthesis technology

Inactive Publication Date: 2009-09-09
CHINA LUCKY FILM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The compound first appeared in the Japanese patent in 2001, and its patent number is JP2001209144. This patent is an application patent, which discloses that the compound is used as a nucleating agent in thermal developing materials, but does not disclose the synthesis of the compound , and the relevant synthetic methods have not been seen in any published literature and patents

Method used

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  • Method for preparing compound of 1, 2 (dodecyl) 4 hydroxide methylene - 3, 5 pyrazole
  • Method for preparing compound of 1, 2 (dodecyl) 4 hydroxide methylene - 3, 5 pyrazole
  • Method for preparing compound of 1, 2 (dodecyl) 4 hydroxide methylene - 3, 5 pyrazole

Examples

Experimental program
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Effect test

Embodiment 1

[0021] In a 1000mL three-necked flask, add 105ml of dodecanal, 45g of calcium oxide, 15ml of hydrazine hydrate (85% content) and 120mL of absolute ethanol, reflux reaction for 2 hours, cooling, and precipitate 64g of intermediate A, yield 73 %;

[0022] 64 grams of intermediate A and 17.5 grams of lithium aluminum hydride were refluxed in 600 milliliters of anhydrous ether for 2 hours, and 10% aqueous sodium hydroxide solution was added until no obvious hydrogen gas was released. After cooling, 60 grams of white solid was precipitated, which was intermediate B , yield 93%;

[0023] 60 grams of intermediate B and 17.5 grams of 30% sodium hydride, 39 milliliters of diethyl malonate were refluxed in 140 milliliters of chlorobenzene for 5 hours, and the ethanol generated in the reaction was evaporated under reduced pressure, and 265 milliliters of dichloromethane and 265 milliliters of water was extracted, and 2N hydrochloric acid was added to the extract to adjust the pH value t...

Embodiment 2

[0030] In a 500mL three-neck flask, add 53ml of dodecanal, 23g of calcium oxide, 8ml of hydrazine hydrate (85% content) and 80mL of methanol, reflux for 1.5 hours, cool, and precipitate 30g of intermediate A, with a yield of 68%;

[0031] 30 grams of intermediate A and 8.4 grams of lithium aluminum hydride were refluxed in 250 ml of anhydrous ether for 1 hour, and 15% potassium hydroxide aqueous solution was added until no obvious hydrogen gas was released. After cooling, 28 grams of white solid were precipitated, which was intermediate B , yield 92%;

[0032] 28 grams of intermediate B and 8.4 grams of 30% sodium hydride, 18 milliliters of diethyl malonate were refluxed in 70 milliliters of toluene for 4.5 hours, and the ethanol generated in the reaction was evaporated under reduced pressure, and 120 milliliters of chloroform and 120 milliliter of water for extraction, adding 1N sulfuric acid to the extract to adjust the pH value to 4.5, and 19.7 grams of intermediate C were ...

Embodiment 3

[0039] In a 500mL three-necked flask, add 60 milliliters of dodecanal, 26 grams of calcium oxide, 10 milliliters of hydrazine hydrate (85% content) and 70 milliliters of dehydrated ethanol, reflux for 1 hour, cool, and separate out 35 grams of intermediate A with a yield of 70 %;

[0040] 35 grams of intermediate A and 10 grams of lithium aluminum hydride were refluxed in 350 milliliters of anhydrous ether for 2 hours, and 10% aqueous sodium hydroxide solution was added until no obvious hydrogen gas was released. After cooling, 32 grams of white solid were precipitated, which was intermediate B , yield 91%;

[0041] 32 grams of intermediate B and 10 grams of 30% sodium hydride, 21 milliliters of diethyl malonate were refluxed in 80 milliliters of xylene for 4 hours, and the ethanol generated in the reaction was evaporated under reduced pressure, and 150 milliliters of normal hexane and 100 Milliliter of water was extracted, and 50% glacial acetic acid was added to the extract...

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Abstract

A kind of 1, the preparation method of 2-two (dodecyl)-4-hydroxymethylene foridene-3,5-pyrazoline diketone compound, it comprises the following steps: 1. add dodecanal, oxidize Calcium, hydrazine hydrate and alcohol, reflux reaction for 1 to 2 hours, to obtain intermediate A; ② intermediate A, anhydrous ether and lithium aluminum hydride, reflux reaction for 1 to 2 hours, neutralization, to obtain intermediate B; ③ intermediate B Reflux reaction with sodium hydride and diethyl malonate in an organic solvent for 4 to 5 hours, remove the generated ethanol, neutralize, and obtain intermediate C; ④Reaction of intermediate C with triethyl orthoformate in acetic anhydride 2 ~3 hours, the reaction temperature is 70~90 ℃, obtains 1,2-di(dodecyl)-4-hydroxymethylidene-3,5-pyrazoline dione compound; the present invention has advanced technology and simple aftertreatment , The obtained product has high purity.

Description

technical field [0001] The present invention relates to a preparation method of pyrazoline diketone compounds, in particular to 1,2-di(dodecyl)-4-hydroxymethylidene-3,5-pyrazole used in thermal development materials Process for the preparation of phenedione compounds. Background technique [0002] As we all know, among various types of nucleating agents for heat-developing materials, there is a pyrazolidinedione derivative whose structural formula is as follows: [0003] [0004] The compound first appeared in the Japanese patent in 2001, and its patent number is JP2001209144. This patent is an application patent, which discloses that the compound is used as a nucleating agent in thermal imaging materials, but does not disclose the synthesis of the compound , and the relevant synthetic methods have not been seen in any published literature and patents. Contents of the invention [0005] The problem to be solved by the present invention is to provide a kind of 1,2-di(d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/36
Inventor 杨玉琴申跃生
Owner CHINA LUCKY FILM CORP
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