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Process for preparation of n,n-di substituted carboxamides

A disubstituted, carboxamide compound technology, applied in the direction of carboxylic acid amide preparation, organic compound preparation, chemical instruments and methods, etc., can solve problems such as difficult to apply on an industrial scale

Inactive Publication Date: 2014-10-22
DIRECTOR GENERAL DEFENCE RES & DEV ORG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantages of this method are:
This is difficult to apply on an industrial scale

Method used

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  • Process for preparation of n,n-di substituted carboxamides
  • Process for preparation of n,n-di substituted carboxamides
  • Process for preparation of n,n-di substituted carboxamides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Preparation of N,N-diethyl-2-phenylacetamide (DEPA)

[0097] 136 g (1 mole) of phenylacetic acid and 136 g (=127 ml, 1 mole) of N,N-diethylcarbamoyl chloride were placed in a 1-liter two-neck round bottom flask equipped with an air condenser placed on a magnetic stirrer. Add 98 g (96 ml, 1.2 moles) of 1-methylimidazole (an organic tertiary base) to the above 1 L two-neck round bottom flask at room temperature using a pressure equalizing funnel fitted into the side neck of the round bottom flask . After the addition was complete, the reaction mixture was stirred continuously for 30 minutes at room temperature. Then, the reaction mixture was treated with 250 ml of water and the two layers were separated. The pure and colorless product N,N-diethyl-2-phenylacetamide (DEPA) was obtained by vacuum distillation of the organic layer.

[0098] The purity of the compound was analyzed using GC-MS and the purity of the compound was greater than 99.5%. And, the yield of product ...

Embodiment 2

[0101] Preparation of N,N-diethyl-m-toluamide (DEET)

[0102] Put 136g (1 mole) of m-toluic acid (3-methylbenzoic acid) and 136g (=127ml, 1 mole) of N,N-diethylcarbamoyl chloride into a magnetic stirrer equipped with air condensing in a 1-liter two-necked round-bottom flask. At room temperature, 121 g (167 ml, 1.2 moles) of triethylamine (an organic tertiary base) was added to the above 1 liter two-neck round bottom flask using a pressure equalizing funnel fitted in the side neck of the round bottom flask. After the addition was complete, the reaction mixture was stirred continuously at room temperature for 20 minutes. Then, the reaction mixture was treated with 250 ml of water and the two layers were separated. The pure and colorless product N,N-diethyl-m-toluamide (DEET) was obtained by vacuum distillation of the organic layer.

[0103] The purity of the compound was analyzed using GC-MS and the purity of the compound was greater than 99.5%. The yield of the product was ...

Embodiment 3

[0106] Preparation of N,N-diethylbenzamide (DEB)

[0107] 122 g (1 mole) of benzoic acid and 136 g (=127 ml, 1 mole) of N,N-diethylcarbamoyl chloride were placed in a 1-liter two-neck round bottom flask equipped with an air condenser placed on a magnetic stirrer. At room temperature, 222 g (285 ml, 1.2 moles) of tributylamine was added to the above-mentioned 1-liter two-necked round-bottomed flask using an equalizing funnel fitted in the side neck of the round-bottomed flask. After the addition was complete, the reaction mixture was stirred continuously at room temperature for 20 minutes. Then, the reaction mixture was treated with 250 ml of water and the two layers were separated. The pure and colorless product N,N-diethylbenzamide (DEB) was obtained by vacuum distillation of the organic layer.

[0108] The purity of the compound was analyzed using GC-MS and the purity of the compound was greater than 99.5%. The yield of the product was 173 g (98%).

[0109]

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Abstract

The present disclosure relates to a single pot process for preparation of a N,N-di substituted carboxamide compounds of formula (I), said process comprising: reacting a carboxylic acid with a di-substituted carbamoyl chloride in presence of an organic tertiary base to obtain the N,N-di substituted carboxamide compounds of formula (I). The process of the present disclosure involves a simple step, and it is energy and time saving process for preparation of N, N-di substituted carboxamides.

Description

technical field [0001] The present disclosure relates to a one-pot process for the preparation of N,N-disubstituted carboxamides. The method of the present disclosure is an energy-efficient and time-saving method. Background technique [0002] Amides or carboxamides are important commercial, biological, pharmaceutical and agricultural chemicals. Amides are widely used as colorants in crayons, pencils and inks, in the paper industry, plastics and rubber industries, and in water and sewage treatment. Acetaminophen (an amide) is used as an analgesic (pain reliever). Acetaminophen is used as an active ingredient in products such as Amadil, Datril, Cetadol, Naprinol, Tylenol and Panadol. Another example of an amide analgesic is phenacetin used in products such as Empirin (amprin) and APC (aspirin, phenacetin and caffeine) tablets. Other commercially used amides include: DEB, DEPA, and DEET used as insect repellents; , Miltown) ((Mebuurea, Miproton)); and Sevin (Carbaryl) and...

Claims

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Application Information

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IPC IPC(8): C07C231/10C07C231/12C07D215/54C07D295/215
CPCC07D295/215C07C231/12C07C231/10C07D213/82C07D295/195C07C233/65C07C233/11C07C233/05C07C231/14
Inventor 阿姆霸提·纳拉辛哈·劳库马兰·加内桑拉贾戈帕兰·维贾雅拉加万
Owner DIRECTOR GENERAL DEFENCE RES & DEV ORG
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