Synthesizing method for amide compound

A technology of amide compounds and synthesis methods, applied in the preparation of organic compounds, formation/introduction of amide groups, chemical instruments and methods, etc., can solve problems such as difficult separation, corrosion, and large amount of condensing agent, and achieve mild reaction conditions , raw materials are cheap and easy to obtain, and the effect of post-processing is simple

Active Publication Date: 2015-06-17
ZHEJIANG UNIV OF TECH
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Problems solved by technology

The Beckmann rearrangement method uses oxime as a raw material and is obtained through Beckmann rearrangement; the disadvantage of this method is that the commonly used Beckmann rearrangement reagents are mostly sulfuric acid, phosphorus pentachloride, and Beckmann reagent (hydrogen chloride in acetic acid-acetic anhydride) solution), polyphosphoric acid and some acid halides and other strong corrosive substances, polluting the environment
The condensation method is catalyzed by condensation agents such as excess dicyclohexylsuccinimide (DCC), diisopropylsuccinimide (DIC), and 1-hydroxy-benzo-triazole (HOBT). Under this method, the carboxylic acid generates an active ester intermediate, reacts with an amine to form an amide, and simultaneously produces an equal amount of difficult-to-separate urea compounds (DCU, DIU, etc.); the significant disadvantage of this method is that the amount of condensing agent is large, the price is expensive, and it cannot be recycled. , converted into urea compounds that are difficult to separate after the reaction
Another method is to react carboxylic acid with thionyl chloride to generate acid chloride, and then react with amine to generate ester in the presence of acid-binding agent; the disadvantage of this method is that gases such as hydrogen chloride and sulfur dioxide will , seriously corrode and pollute the environment; at the same time, since the acid chloride has to be purified by distillation, the operation steps are increased, and the total production cost is high

Method used

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  • Synthesizing method for amide compound
  • Synthesizing method for amide compound
  • Synthesizing method for amide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the preparation of N-n-butyl-benzamide (III-1)

[0031] The reaction formula is as follows:

[0032]

[0033] Under air atmosphere, add 0.005g (2.5‰mmol Ru) Ru / C catalyst to the reaction flask, then add 98μL (1mmol) n-butylamine (II-1), 10mL ethanol, and then mix 117μL (1mmol ) phenylacetonitrile (I-1) was added into the reaction flask, the temperature was kept at about 20° C., the reaction was stirred for 36 hours, and the reaction was monitored, and the raw material (I-1) basically reacted completely. After the reaction is finished, filter, wash the filter residue twice with ethanol, combine the filtrate, dry, concentrate, thin-layer chromatography (ethyl acetate / petroleum ether=1 / 5), obtain the N-normal compound shown in formula (III-1). Butyl-benzamide 0.149g, yellow solid, yield 84%, purity 98%. The structural representation of compound formula (III-1) is as follows:

[0034] 1 H NMR (600MHz, CDCl 3 )δ7.77-7.75(t,2H),7.49-7.46(t,1H),7.49-7.40(...

Embodiment 2

[0035] Embodiment 2: the preparation of N-n-butyl-benzamide (III-1)

[0036] Under air atmosphere, add 0.01g (5‰mmol Ru) Ru / C catalyst to the reaction flask, then add 98μL (1mmol) n-butylamine (II-1), 10mL ethanol, and then mix 117μL (1mmol ) phenylacetonitrile (I-1) was added in the reaction flask, the temperature was kept at about 20°C, and the reaction was stirred for 24 hours, and the reaction was monitored, and the raw material (I-1) basically reacted completely. Filter after the reaction finishes, wash the filter residue with ethanol twice, combine the filtrate, dry the organic phase, concentrate, thin-layer chromatography (ethyl acetate / petroleum ether=1 / 5), obtain the N shown in formula (III-1). -n-butyl-benzamide 0.152g, yield 86%, purity 98%.

Embodiment 3

[0037] Embodiment 3: the preparation of N-n-butyl-benzamide (III-1)

[0038] Under air atmosphere, add 0.005g (2.5‰mmol Ru) Ru / C catalyst to the reaction flask, then add 98μL (1mmol) n-butylamine (II-1), 10mL THF, and then mix 117μL (1mmol ) phenylacetonitrile (I-1) was added into the reaction flask, the temperature was kept at about 20° C., the reaction was stirred for 25 hours, and the reaction was monitored, and the raw material (I-1) basically reacted completely. Filter after the reaction is over, wash the filter residue twice with dichloromethane, combine the filtrates, extract twice with dichloromethane / water (30mL / 30mL) system, dry the organic phase, concentrate, thin-layer chromatography (ethyl acetate / petroleum ether= 1 / 5) to obtain 0.156 g of N-n-butyl-benzamide represented by formula (III-1), with a yield of 88% and a purity of 98%.

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Abstract

The invention discloses a synthesizing method for an amide compound shown in formula (III). The synthesizing method comprises the following steps: adopting replacing acetonitrile shown in formula (I) and amines compound shown in formula (II) as raw materials in air atmosphere; adopting Ru/C as a catalyst; conducting reaction in solvent to generate the amide compound shown in formula (III); the solvent is one selected from ethyl alcohol, furanidine, methyl sulfoxide and o-dichlorobenzene. The synthesizing method being novel synthesizing route is simple to operate, convenient in post-treatment, high in product yield, and good in product purity; particularly, the catalyst and the solvent can be used repeatedly; air is taken as oxidant; not only production cost is reduced, but also the method is environmental-friendly, and very suitable for large-scale industrialization production.

Description

technical field [0001] The present invention relates to a method for synthesizing amide compounds represented by formula (III); [0002] Background technique [0003] Amide can be regarded as a compound formed by the condensation of carboxylic acid and ammonia or amine, which is a type of carboxylic acid derivative, and can also be regarded as a derivative in which the hydrogen of ammonia (or amine) is replaced by an acyl group. Amide compounds have important industrial uses and belong to a class of bulk industrial intermediates. Many drugs are themselves amides. [0004] There are many synthetic methods of amides, among which the classic synthetic methods include Beckmann rearrangement, condensation, acid chloride and so on. The Beckmann rearrangement method uses oxime as a raw material and is obtained through Beckmann rearrangement; the disadvantage of this method is that the commonly used Beckmann rearrangement reagents are mostly sulfuric acid, phosphorus pentachlor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/06C07C233/65C07C231/10C07C233/73C07D277/68C07D213/82C07D203/18
CPCY02P20/584
Inventor 王宇光朱冰春吴中礼李钦
Owner ZHEJIANG UNIV OF TECH
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