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Method of substituting formamide with vitride reduction cycle

A technology of formamide and red aluminum, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of amino compounds, etc., can solve problems such as high cost, complicated treatment process, and high price

Active Publication Date: 2013-06-26
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since Lithium Aluminum Hydride is a highly active reducing agent, it will cause combustion if it is exposed to air for a few minutes, especially in relatively humid air, it usually catches fire immediately, and it is expensive, making it impossible to scale and continuous production
When using the system of sodium borohydride / iodine, the molar ratio of sodium borohydride: iodine: formamide usually reaches 3:1:1, and the cost is high; the product purity is low, the impurity content is relatively large, and the yield is about 50%; The recovery cost of industrial wastewater containing iodine is high, and the treatment process is relatively complicated

Method used

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  • Method of substituting formamide with vitride reduction cycle
  • Method of substituting formamide with vitride reduction cycle
  • Method of substituting formamide with vitride reduction cycle

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1N, N-dimethylcyclohexylformamide is reduced to N, N-dimethylcyclohexylmethylamine

[0024] 1) Under argon protection, add 40g of N,N-dimethylcyclohexylformamide and 480g of THF to a clean and dry three-necked flask, stir mechanically and cool down to 0°C, and add 149g of red Aluminum (70% toluene solution), keep warm at 25-30°C after dropping, after TLC (ethyl acetate, glacial acetic acid development, iodine fumigation) detects that there is no raw material remaining, then cool down to 0°C.

[0025] 2) Under the protection of argon, add 41.2g of sodium hydroxide and 165g of water into a clean and dry three-necked flask, stir until fully dissolved, and cool down to an internal temperature of less than 5°C. Add the reaction solution in (1) dropwise at an internal temperature of 0-30°C, and keep it warm at 20-30°C for 1 hour after the drop is complete. After the reaction is complete, let it stand for 10 minutes before separating the liquids, extract the aqueous...

Embodiment 2

[0026] Embodiment 2N, N-diethylbenzamide is reduced to N, N-diethylbenzylamine

[0027] 1) Under the protection of argon, add 45.6g N,N-diethylphenylformamide and 547g THF to a clean and dry three-necked flask, stir mechanically and cool down to 0°C, and add 163.9 g red aluminum (70% toluene solution), keep the temperature at 25-30°C after dropping, and cool down to 0°C after TLC detects that there is no raw material remaining.

[0028] 2) Under the protection of argon, add 45.4g of sodium hydroxide and 180g of water into a clean and dry three-necked flask, stir until fully dissolved, and cool down to an inner temperature of less than 5°C. Add the reaction solution in (1) dropwise at an internal temperature of 0-30°C, and keep it warm at 20-30°C for 1 hour after the drop is complete. After the reaction is complete, let it stand for 10 minutes before separating the liquids, extract the aqueous phase with 160g of ethyl acetate, and wash the organic phase with water. to PH≈7. T...

Embodiment 3

[0029] Embodiment 3N-methyl-N-tert-butylbenzamide is reduced to N-methyl-N-tert-butylbenzylamine

[0030] 1) Under the protection of argon, add 49.3g of N-methyl-N-tert-butylbenzamide and 591g of THF into a clean and dry three-necked flask, stir mechanically and lower the temperature to 0°C, and control the internal temperature from 0 to 30°C to drop Add 186g of red aluminum (70% toluene solution), keep the temperature at 25-30°C after dropping, and cool down to 0°C after TLC detection that there is no raw material remaining.

[0031] 2) Under the protection of argon, add 51.5g of sodium hydroxide and 200g of water into a clean and dry three-necked flask, stir until fully dissolved, and cool down to an inner temperature of less than 5°C. Add the reaction solution in (1) dropwise at an internal temperature of 0-30°C, and keep it warm at 20-30°C for 1 hour after the drop is complete. After the reaction is complete, let it stand for 10 minutes before separating the liquids, extra...

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Abstract

The invention relates to a method of substituting formamide with vitride reduction cycle. The mole ratio of the vitride to the cyclo-substituted formamide is 1.5-3. The method comprises the following steps: taking methyl benzene or tetrahydrofuran as a reaction solvent, adopting a reverse dropwise addition manner, namely dropwise adding the vitride solution into the cyclo-substituted formamide solution at the temperature of 0-30 DEG C, hydrolyzing the reaction liquid with sodium hydroxide after the reaction is finished, extracting the aqueous phase with ethyl acetate after the hydrolysis is finished, combining the organic phase and rinsing, decompressing to remove the solvent to obtain a crude cyclo-substituted formamide product, continuing decompression and distilling to obtain refined cyclo-substituted formamide product. Compared with a lithium aluminum hydride process and a sodium boronhydride / iodine process, the method has the advantages of being low in cost, high in conversion rate, mild in reaction conditions, and suitable for large-scale and continuous production.

Description

technical field [0001] The invention relates to a method for replacing formamide with a red aluminum reducing ring, which belongs to the field of organic synthesis. Background technique [0002] Ring substituted amines with the following general structure: [0003] [0004] where R 1 It can be a benzene ring or a cycloalkane with 5 to 8 carbons; R 2 and R 3 Is H, straight chain or branched chain alkyl, R 2 and R 3 They may be the same or different. [0005] Amines of this structure are derived from the reduction of ring-substituted formamides and have the following structure: [0006] [0007] where R 1 It can be a benzene ring, a cycloalkane with 5 to 8 carbons; R 2 and R 3 Is H, straight chain or branched chain alkyl, R 2 and R 3 They may be the same or different. [0008] The existing literature mainly uses lithium aluminum tetrahydride (such as WO2008153207) or sodium borohydride / iodine (Tetrahedron Vol. 48:4623-4628) to reduce ring-substituted carboxam...

Claims

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Application Information

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IPC IPC(8): C07C209/50C07C211/17C07C211/27
Inventor 柏忠源石运兴王权李鹏徐海源李宁王春勇
Owner VALIANT CO LTD
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