N,N'-dialkyl dithiooxamide as well as preparation method and application thereof

A technology of dialkyldithiooxamide and oxamide, applied in the N field, can solve the problems of cumbersome operation, complicated operation, expensive raw material and the like, and achieves low raw material and manufacturing cost, high reaction yield and low price. Effect

Active Publication Date: 2014-11-19
HUNAN CHEMAPI BIOLOGICAL TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The above preparation process has the disadvantages of scarce source of raw materials, expensive raw materials, complex preparation process equipment, some raw materials involve high-pressure gas, complicated operation, and some use toxic and harmful raw materials, and some also report that they need to use chromatography columns. Separation, cumbersome operation, low product purity, unfavorable for industrial production

Method used

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  • N,N'-dialkyl dithiooxamide as well as preparation method and application thereof
  • N,N'-dialkyl dithiooxamide as well as preparation method and application thereof
  • N,N'-dialkyl dithiooxamide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of N, N'-di-n-butyldithiooxamide

[0043] The first preparation method of N,N'-di-n-butyl oxamide is to add n-butylamine 40g, pyridine 44.3 g and toluene 400mL, after stirring evenly, cool to 0-5°C with an ice-salt bath, and slowly add 33g of oxalyl chloride dropwise. Then reacted at room temperature for 4 hours, filtered to obtain a light orange solid, washed twice with dilute hydrochloric acid, dried after washing with water, concentrated and filtered to obtain 39 g of white crystal N, N'-di-n-butyl oxalamide, yield 75%, melting point 157 ~158°C;

[0044] Preparation method 2 of N,N'-di-n-butyl oxalamide: Add 500mL of toluene and 153g of n-butylamine into the reaction bottle, slowly add 140g of diethyl oxalate under stirring, heat up to reflux, the reaction produces ethanol, and the reflux temperature is 90 ℃, reflux reaction for 3 hours, the reflux device is a distillation device, slowly distill out the by-product ethanol to make the reaction complete, ...

Embodiment 2

[0048] Embodiment 2: the preparation of N, N'-didodecyl dithiooxamide

[0049] N, N'-didodecyl oxalamide preparation method 1, add n-dodecylamine 190g in the three-necked bottle equipped with a stirrer, a reflux condenser with a drying tube and an exhaust gas absorption device, and a dropping funnel, three 104g of ethylamine and 1000mL of toluene were stirred evenly, cooled to 0-5°C with an ice-salt bath, and 63.5g of oxalyl chloride was slowly added dropwise. Then reacted at room temperature for 4 hours, filtered to obtain a light orange solid, washed twice with dilute hydrochloric acid, dried after washing with water, concentrated and filtered to obtain 180.5 g of white crystal N, N'-didodecyl oxalamide, yield 85%, Melting point 123~124℃;

[0050]Preparation method 2 of N, N'-didodecyl oxalamide: Add 1000 mL of toluene and 190 g of n-dodecylamine into the reaction flask, slowly add 59 g of dimethyl oxalate under stirring, heat up to reflux, the reaction produces methanol, a...

Embodiment 3

[0053] Embodiment 3: the preparation of N, N'-dibenzyl dithiooxamide

[0054] N, N'-dibenzyl oxamide preparation method 1, add benzylamine 110g, triethylamine 103.7g in the three-neck bottle equipped with agitator, reflux condenser with drying tube and tail gas absorption device, dropping funnel and 550mL of toluene, stirred evenly, cooled to 0-5°C with an ice-salt bath, and slowly added 63.5g of oxalyl chloride dropwise. Then reacted at room temperature for 4 hours, filtered to obtain a light orange solid, washed twice with dilute hydrochloric acid, dried after washing with water, concentrated and filtered to obtain 111.3 g of white crystal N, N'-dibenzyl oxalamide, yield 83%, melting point 224 ~225°C;

[0055] Preparation method 2 of N,N'-dibenzyloxalamide: Add 550mL of toluene and 110g of benzylamine into the reaction flask, slowly add 59g of dimethyl oxalate under stirring, heat up to reflux, the reaction produces methanol, and the reflux temperature is about 90°C. Reflu...

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Abstract

The invention discloses N,N'-dialkyl dithiooxamide as well as a preparation method and application thereof. The preparation method comprises the following steps: reacting diester oxalate or oxalyl chloride with amine to generate N,N'-disubstituted oxamide; and generating the N,N'-dialkyl dithiooxamide under the action of a vulcanization reagent. According to the preparation method of the N,N'-dialkyl dithiooxamide, the N,N'-disubstituted oxamide is generated by reacting the diester oxalate or the oxalyl chloride with the amine, and the N,N'-dialkyl dithiooxamide is generated under the action of the vulcanization reagent. The N,N'-dialkyl dithiooxamide is taken as an antioxidant, a herbicide, a sterilizing agent, an analgesic, an anti-tuberculosis, a precious metal platinum-palladium analysis reagent and the like. The preparation method has the advantages of adoption of readily-available raw materials, low price of a finished product, easiness and convenience in operation under the normal pressure, realization of production without special equipment, high reaction yield, low raw material and manufacturing costs, freeness from chromatographic column separation, and purity of up to 99 percent through simple recrystallization.

Description

technical field [0001] The invention relates to the technical field of preparation of sulfur-containing compounds, in particular to an N, N'-dialkyldithiooxamide and a preparation method thereof. Background technique [0002] N, N'-disubstituted dithiooxamides are a class of sulfur-containing compounds with a wide range of uses, and can be used as antioxidants, herbicides, fungicides, analgesics, anti-tuberculosis agents, precious metal platinum palladium analysis reagents, etc. . In recent years, people have been active in the research on this kind of compounds. [0003] The existing process for preparing this type of compound is illustrated by taking didodecanyl dithiooxamide as an example, and the existing synthetic technical route is as follows. Journal of Organic Chemistry; vol. 26; (1961); p. 3980–3987 reads: [0004] [0005] DE2246025 reports the following route: [0006] [0007] US2525075 reports the following route: [0008] [0009] The above prepar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C333/16C07D211/58
Inventor 范荣李加前
Owner HUNAN CHEMAPI BIOLOGICAL TECH
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