Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of synthetic method of nitroacrylamide compound

A technology for nitroacrylamide and acrylamide, which is applied in the field of organic compound synthesis, can solve the problems of cumbersome reaction steps, harsh conditions, low product yield and the like, and achieves simple operation, mild reaction conditions, and strong substrate universality. Effect

Active Publication Date: 2017-12-05
ZHEJIANG UNIV OF TECH
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the synthesis methods of nitroacrylamide compounds reported at home and abroad mainly include the following methods: 1. N,N-dimethyl-2-hydroxyl-3-nitropropionamide is eliminated to generate the target product nitro Acrylamide compounds (see Organic Letters, 12(5), 1024-1027; 2010), the reaction steps of this method are cumbersome and need to be carried out at -20°C, and the conditions are harsh; 2. N,N-diethylacrylamide is brominated , nitration to obtain the target product N, N-diethyl-3-nitropropionamide (referring to Tetrahedron Letters, 42 (28), 4709-4712; 2001), this method needs to use highly toxic substance liquid bromine; 3.N -Methyl-N'-methoxyl-2-carbonylacetamide reacts with nitromethane to synthesize target product N-methyl-N'-methoxyl-3-nitropropionamide (see Journal of the American Chemical Society , 132(12), 4036-4037; 2010), the yield of this method is low

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of nitroacrylamide compound
  • A kind of synthetic method of nitroacrylamide compound
  • A kind of synthetic method of nitroacrylamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] 0.5mmol N-methyl-N'-benzenesulfonyl-2-methacrylamide (119.5mg), 1.0mmolN CS (N-chlorosuccinimide) (133.5mg), 1.0mmolAgNO 2 (154.0 mg), 5 mL of acetonitrile were added to a 15 mL reaction tube. Next, it was magnetically stirred at 80° C. for 12 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure. The residue was packed into a column, and then separated by column chromatography. : 1 mixed solvent as eluent, collect the eluent containing product, and the eluent evaporates solvent to obtain pure product N-methyl-N'-benzenesulfonyl-2-methyl-3-nitropropene amides. The material was a pale yellow solid in 85% yield.

[0028] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ7.88–7.86(d,J=7.5Hz,2H),7.72–7.68(m,1H),7.60–7.54(m,2H),6.85–6.84(d,J=1.5Hz,1H), 3.31(s,3H),2.28–2.27(d,J=1.5Hz,3H).

Embodiment 2

[0030]

[0031] 0.5mmol N-methyl-N'-benzenesulfonyl-2-methacrylamide (119.5mg), 1.0mmolN CS (chlorosuccinimide) (133.5mg), 1.0mmolAgNO 2 (154.0 mg), 5 mL of acetonitrile were added to a 15 mL reaction tube. Next, magnetic stirring was performed at 100° C. for 12 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure. The residue was packed into a column, and then separated by column chromatography. : 1 mixed solvent as eluent, collect the eluent containing product, and the eluent evaporates solvent to obtain pure product N-methyl-N'-benzenesulfonyl-2-methyl-3-nitropropene amides. The material was a pale yellow solid in 80% yield.

[0032] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ7.88–7.86(d,J=7.5Hz,2H),7.72–7.68(m,1H),7.60–7.54(m,2H),6.85–6.84(d,J=1.5Hz,1H), 3.31(s,3H),2.28–2.27(d,J=1.5Hz,3H).

Embodiment 3

[0034]

[0035] 0.5mmol N-methyl-N'-benzenesulfonyl-2-methacrylamide (119.5mg), 1.0mmolN CS (chlorosuccinimide) (133.5mg), 1.0mmolAgNO 2(154.0 mg), 5 mL of acetonitrile were added to a 15 mL reaction tube. Next, it was magnetically stirred at 50° C. for 12 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure. The residue was packed into a column, and then separated by column chromatography. : 1 mixed solvent as eluent, collect the eluent containing product, and the eluent evaporates solvent to obtain pure product N-methyl-N'-benzenesulfonyl-2-methyl-3-nitropropene amides. The material was a light yellow solid, 50% yield.

[0036] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ7.88–7.86(d,J=7.5Hz,2H),7.72–7.68(m,1H),7.60–7.54(m,2H),6.85–6.84(d,J=1.5Hz,1H), 3.31(s,3H),2.28–2.27(d,J=1.5Hz,3H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthetic method of a nitro acrylamides compound shown in a formula II. The method comprises the following steps: an acrylamides compound shown in a formula I, N-chlorosuccinimide, and AgNO2 are added in an organic solvent, the materials are reacted for 5-20 hours at the temperature of 25-100 DEG C, and the nitro acrylamides compound shown in the formula II is obtained by separating and purifying an obtained reaction solution. A nitrogen source system has the advantages of low cost, easy acquisition, little toxicity, environment friendliness, mild reaction condition, good universality of the function group, and simple operation.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing nitroacrylamide compounds. (2) Background technology [0002] Acrylamide is an important raw material for organic synthesis, and can be used as an intermediate in the synthesis of medicines, pesticides, dyes and paints. The main industrial uses of acrylamide compound monomers are the synthesis of dyes, the synthesis of plastics and adhesives, and are widely used in paper, textile and plastic industries. It can also be used as a slurry for building dam foundations, tunnels and sewage pipes, and as a thickener for soaps and cosmetics. In the field of biochemical analysis, acrylamide compounds are also used for gel electrophoresis determination of nucleic acids and proteins. Acrylamide compounds can also be used to produce polyacrylamide compounds and other copolymerized compounds to meet different needs. These polymers are widely used in...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/40C07C311/16
Inventor 刘运奎任少波汪衡
Owner ZHEJIANG UNIV OF TECH