Method for preparing compound 2-N, N-dimethylaminodithioformic acid-2, 3-dihydro-1, 4-dioxane

A technology of dimethyl dithiocarbamate and sodium dimethyl dithiocarbamate, applied in organic chemistry and other fields

Inactive Publication Date: 2012-07-04
NINGBO UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For the synthetic method of preparing compound 3 from compound 1, the synthetic route of existing literature needs two steps and the second step needs to be refluxed in toluene for 15 hours to complete, the reaction Longer time and additional reflux in toluene was required, the overall yield from compound 1 to compound 3 was 70.3%

Method used

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  • Method for preparing compound 2-N, N-dimethylaminodithioformic acid-2, 3-dihydro-1, 4-dioxane
  • Method for preparing compound 2-N, N-dimethylaminodithioformic acid-2, 3-dihydro-1, 4-dioxane

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Experimental program
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Embodiment 1

[0016] 2,3-dichloro-1,4-dioxane (40.65 g, 0.26 mol), NaSCSN (CH 3 ) 2 .2H 2 O (49.8 grams, 0.35 moles) and sodium hydroxide (5 grams, 0.125 moles) in DMF (200 milliliters) were slowly heated to 70 DEG C in a there-necked flask, and stirred at this temperature for 3 hours, a large amount of solids were separated out, The resulting solid was filtered, then the solid was dissolved in chloroform, washed three times with saturated brine, then washed twice with water, dried over anhydrous magnesium sulfate, and the chloroform was removed to obtain 2-N,N-dimethyl in the form of colorless crystals. Dithiocarbamate-2,3-dihydro-1,4-dioxane (47 g, 77% yield).

[0017] The melting point is 170-171°C;

[0018] 1 H-NMR (CDCl 3 , 400Hz) 6.47 (s, 1H), 4.28-4.30 (m, 2H), 4.19-4.21 (m, 2H), 3.53 (s, 3H), 3.39 (s, 3H).

[0019] 13 C-NMR 195.2 137.5, 128.2 64.8, 84.2, 45.5, 41.7.

Embodiment 2

[0021] 2,3-dichloro-1,4-dioxane (40.65 g, 0.26 mol), NaSCSN (CH 3 ) 2 .2H 2 O (49.8 grams, 0.35 moles) and sodium hydroxide (1 gram, 0.025 moles) were slowly heated to 70° C. in a three-necked flask in DMF (200 milliliters), and stirred at this temperature for 3 hours, a large amount of solids were separated out, The resulting solid was filtered, then the solid was dissolved in chloroform, washed three times with saturated brine, then washed twice with water, dried over anhydrous magnesium sulfate, and the chloroform was removed to obtain 2-N,N-dimethyl in the form of colorless crystals. Dithiocarbamate-2,3-dihydro-1,4-dioxane (47 g, 77% yield).

[0022] The melting point is 170-171°C;

[0023] 1 H-NMR (CDCl 3 , 400Hz) 6.47 (s, 1H), 4.28-4.30 (m, 2H), 4.19-4.21 (m, 2H), 3.53 (s, 3H), 3.39 (s, 3H).

[0024] 13 C-NMR 195.2 137.5, 128.2 64.8, 84.2, 45.5, 41.7.

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Abstract

The invention relates to a method for preparing 2-N,N-sodium dimethyl dithio carbamate-2,3-dihydro-1,4-dioxane by reacting 2,3-dichloro-1,4-dioxane with sodium dimethyl dithio carbamate dihydrate. In the method, only one step is required for the reaction by adding sodium hydroxide in the reaction, the reaction time is short, and the yield is high.

Description

technical field [0001] The present invention relates to a kind of preparation method for the important intermediate of electron donor BEDO-TTF, EDO-TTF, more specifically, the present invention relates to 2-N, N-dimethyl dithiocarbamate-2 , The preparation method of 3-dihydro-1,4-dioxane. [0002] Background technique [0003] 2-N, N-dimethyldithiocarbamate-2,3-dihydro-1,4-dioxane (compound 3) is a intermediate, compound 4 is used to prepare the electron donor BEDO-TTF EDO-TTF BEDO-TTF and EDO-TTF are important electron donors for the preparation of organic conductors. HETEROCYCLES, Vol.54, No.2, pp.833-848 has given by 2,3-dichloro-1,4-dioxane (compound 1) through 2,3-N,N-dimethyl Dithiocarbamate-1,4-dioxane (compound 2) prepares 2-N,N-dimethyldithiocarbamate-2,3-dihydro-1,4-dioxane ( The reaction scheme of compound 3), the specific reaction scheme is referred to below. Organic conductors and organic superconductors are important components of molecular electronics...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/12
Inventor 肖勋文沈梁钧刘旭锋王冠南李海云
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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