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A kind of synthetic method of formamide compounds

A synthesis method and formamide technology are applied in the preparation of organic compounds, chemical instruments and methods, preparation of carboxylic acid amides, etc., which can solve the problems of high cost of raw materials and long reaction time, and achieve simple and easy-to-obtain reagents and simple operation. , the effect of low cost

Inactive Publication Date: 2019-03-15
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] But, the raw material cost that the above-mentioned method has is higher, and the reaction time that has is longer

Method used

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  • A kind of synthetic method of formamide compounds
  • A kind of synthetic method of formamide compounds
  • A kind of synthetic method of formamide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of N-cyclohexanecarboxamide

[0030] Add 200mg (1mmol) N-cyclohexane-1-imidazole carboxamide into a 50mL round bottom flask, add 10mL THF to dissolve it, add 5mL of ice water dissolved in 152mg (4mmol) sodium borohydride under vigorous stirring, and detect by TLC Its reaction progress, reaction 30min reaction is complete. In an ice bath, wash with 5% hydrochloric acid, water, 5% sodium carbonate, and water successively, extract once with 80 mL of dichloromethane, wash with saturated brine, and dry over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the crude product was separated and purified by chromatography to obtain 120 mg of the target product, N-cyclohexanecarboxamide, with a yield of 94%. Developing agent: ethyl acetate / petroleum ether=5 / 2, Rf=0.7, color development: potassium permanganate.

[0031] The NMR characterization data of N-cyclohexanecarboxamide is: 1 H NMR (400MHz, CDCl 3 )δ8.05(d, J=14.1Hz, 1H), 6.06(d, J=5...

Embodiment 2

[0033] Synthesis of N-m-toluamide

[0034] Add 450mg (2.2mmol) N-m-toluene-1-imidazole carboxamide into a 50mL round bottom flask, add 10mL THF to dissolve it, add 2mL ice water dissolved in 84mg (2.2mmol) sodium borohydride under vigorous stirring, TLC The progress of the reaction was detected, and the reaction was complete in 25 minutes. In an ice bath, wash with 5% hydrochloric acid, water, 5% sodium carbonate, and water successively, extract once with 80 mL of dichloromethane, wash with saturated brine, and dry over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the crude product was separated and purified by chromatography to obtain 255 mg of the target product, N-m-toluamide, with a yield of 84%. Developing solvent: ethyl acetate / petroleum ether=1 / 1, Rf=0.6, color development: ultraviolet.

[0035] The NMR characterization data of N-m-toluamide is: 1 H NMR (400MHz, CDCl 3 )δ8.74(s,1H),8.68(d,J=11.1Hz,1H),8.34(s,1H),7.83(s,1H),7.40(s,1H),...

Embodiment 3

[0037] Synthesis of N-(3,4-dichlorophenyl)formamide

[0038] Add 400mg (1.6mmol) N-(3,4-dichlorophenyl)-1-imidazole carboxamide into a 50mL round bottom flask, add 10mL THF to dissolve it, add 30mg (0.8mmol) boron dissolved in it under vigorous stirring Sodium hydride ice water 1mL, TLC detects its reaction progress, reacts 30min and reacts completely. In an ice bath, wash with 5% hydrochloric acid, water, 5% sodium carbonate, and water successively, extract once with 80 mL of dichloromethane, wash with saturated brine, and dry over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the crude product was separated and purified by chromatography to obtain 267 mg of the target product N-(3,4-dichlorophenyl)formamide with a yield of 90%. Developing solvent: ethyl acetate / petroleum ether=1 / 1, Rf=0.6, color development: ultraviolet.

[0039] The NMR characterization data of N-(3,4-dichlorophenyl) formamide is: 1 H NMR (400MHz, CDCl 3 )δ8.66(d,J=10.9Hz,...

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Abstract

The invention discloses a method for synthesizing a formamide compound. The synthetic method comprises the following steps: taking carbamyl imidazole compound as a raw material, preparing the formamide compound in a mixed solution of tetrahydrofuran and water by taking hydroboron as a reducing agent. The catalyst hydroboron used in the method disclosed by the invention has the advantages of environment friendliness, stable performance, high conversion rate and the like. Moreover, the initial raw material and used reagents are simple and readily available, the cost is low, and the operation is simple and feasible. Therefore, the route is a route which is low in cost, simple in operation and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing formamide compounds. Background technique [0002] Formamide compounds are important intermediates in the synthesis of nitrogen heterocyclic drugs, and are widely used in the synthesis of substituted aryl imidazoles, fluoroquinolines, 1,2-dihydroquinolines, oxazolidinones and other drugs. Its synthesis is mainly obtained by catalyzing the nitrogen formylation reaction of amine and formic acid. The catalyst used for this reaction mainly contains: HClO 4 -SiO 2 ,TiO 2 -P 25 ,TiO 2 -SO 4 , nanocatalyst MgO, I 2 , VB 1 , encapsulated nano-Fe 2 o 3 Sulfonic acid supported on hydroxyapatite, ZnCl 2 , PEG-400 and ZnO 2 Wait. Some of these catalysts are difficult to prepare, some are expensive, and some have defects such as by-product formation in the preparation. [0003] The synthetic carboxamide compounds reported in the literature mainly contain the following methods: Document 1 (Krishnakumar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/10C07C233/03C07C233/15C07C233/25
CPCC07C231/10C07C233/03C07C233/15C07C233/25
Inventor 滕汉兵周旋陈志勇田泽宇
Owner WUHAN UNIV OF TECH
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