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Preparation method of 1-(2-ethoxyl)-5-mercapto tetrazole

A technology of mercaptotetrazolium and hydroxyethyl, which is applied in the field of preparation of 1--5-mercaptotetrazolium, can solve the problems of high requirements for deprotection conditions, expensive dihydropyran, and low reaction yield. Achieve the effects of low cost, high deprotection yield and high reaction yield

Active Publication Date: 2013-04-24
ZHEJIANG NHU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (3) The improved method of method (2): dithiocarbamate is through hydroxyl protection, then reacts with sodium azide to obtain target product, and the protection reagent that adopts has triphenylchloromethane, isobutylene, acetic anhydride, dihydrogen Pyran, etc., dihydropyran makes the reaction yield as high as 85%, but dihydropyran is expensive and the production cost is high; triphenylchloromethane, isobutylene, and acetic anhydride are used as protective reagents, and the reaction time is long, and the deprotection conditions require High, low reaction yield and other disadvantages

Method used

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  • Preparation method of 1-(2-ethoxyl)-5-mercapto tetrazole
  • Preparation method of 1-(2-ethoxyl)-5-mercapto tetrazole
  • Preparation method of 1-(2-ethoxyl)-5-mercapto tetrazole

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Embodiment 1

[0028] Embodiment 1: Preparation of 2-(trimethylsiloxy)ethanolamine

[0029] Put 61.0g (1.0mol) of ethanolamine into a 250mL four-neck flask equipped with mechanical stirring and a thermometer, add 80.7g (0.5mol) of hexamethyldisilazane dropwise under stirring, and react at 5-50°C for 0.5-2h After the reaction was completed, ammonia gas and light components were extracted under reduced pressure to obtain 133.0 g of 2-(trimethylsilyloxy)ethanolamine with a content of 99.0% and a yield of 98.8%.

Embodiment 2

[0030] Embodiment 2: Preparation of 2-(trimethylsiloxy)ethanolamine

[0031] In a 250mL four-necked flask equipped with mechanical stirring and a thermometer, put 61.0g (1.0mol) of ethanolamine and 108.6g (1.0mol) of trimethylchlorosilane, and react at 5-50°C for 0.5-2h. After the reaction is complete, add toluene 100mL, add 40.0g sodium hydroxide and 100mL water to neutralize the solution, separate layers, wash the toluene layer twice with 100mL water, and recover the solvent under reduced pressure to obtain 131.5g of 2-(trimethylsilyloxy)ethanolamine , content 99.5%, yield 98.2%.

Embodiment 3

[0032] Embodiment 3: Preparation of 2-(trimethylsiloxy)ethanolamine

[0033] In a 250mL four-neck flask equipped with mechanical stirring and a thermometer, put 61.0g (1.0mol) of ethanolamine and 200.1g (1.0mol) of iodotrimethylsilane, and react at 5-50°C for 0.5-2h. After the reaction is complete, add toluene 100mL, add 40.0g sodium hydroxide and 100mL water to neutralize the solution, separate layers, wash the toluene layer twice with 100mL water, and recover the solvent under reduced pressure to obtain 132.0g 2-(trimethylsiloxy)ethanolamine , content 99.0%, yield 98.1%.

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Abstract

The invention discloses a preparation method of 1-(2-ethoxyl)-5-mercapto tetrazole. The existing methods have the defect of high operation cost or low reaction yield. The preparation method disclosed by the invention comprises the following steps: subjecting ethanolamine to react with a silanization reagent to generate 2-(trimethylsiloxy)ethanolamine; in the presence of alcohol and triethylamine,subjecting the 2-(trimethylsiloxy)ethanolamine to react with carbon disulfide to generate N-(2-trimethylsiloxyethyl)triethylamine dithiocarbamate; subjecting the N-(2-trimethylsiloxyethyl)triethylamine dithiocarbamate to react with alkyl halide to generate N-(2-trimethylsiloxyethyl)dithiocarbamate; finally subjecting the N-(2-trimethylsiloxyethyl)dithiocarbamate to undergo azidation reaction and cyclization reaction with sodium azide to generate 1-(2-trimethylsiloxyethyl)-5-mercapto tetrazole; and hydrolyzing the 1-(2-trimethylsiloxyethyl)-5-mercapto tetrazole to obtain the 1-(2-ethoxyl)-5-mercapto tetrazole. The preparation method disclosed by the invention has the advantages of cheap and easily available raw materials, low cost, mild reaction conditions, easiness in operation and high reaction yield.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a preparation method of 1-(2-hydroxyethyl)-5-mercaptotetrazolium. Background technique [0002] At present, 1-(2-hydroxyethyl)-5-mercaptotetrazolium mainly contains the following several synthetic methods: [0003] (1) CN1562980: react metal thiocyanate with benzyl chloride to generate benzyl thiocyanate, and react benzyl thiocyanate with sodium azide to generate 5-benzylthiotetrazolium under the condition of quaternary ammonium salt catalyst , 5-benzylthiotetrazolium is condensed with chloroethanol, and the target product is obtained by debenzylation, with a yield of more than 80%. Metal thiocyanate, metal sodium, liquid ammonia, etc. with high environmental risks are used in the reaction process. The low temperature reaction at -60°C in benzyl also makes the operation cost high. [0004] (2) JP51068568: react ethanolamine with carbon disulfide and an alkylating age...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D257/04
Inventor 李雪明钱洪胜文庆同何晓东鲁国彬
Owner ZHEJIANG NHU CO LTD