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A method for preparing α,α-diamidoalkane compounds with n,n'-dialkylamides

A technology of diamidoalkanes and dialkylamides, which is applied in the preparation of carboxylic acid amides, the preparation of sulfonic acid amides, the preparation of organic compounds, etc. Production and practical applications, etc., to achieve the effect of a wide range of substrates, easy operation, and huge application prospects.

Active Publication Date: 2022-01-11
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the published methods often require the use of reactants with special structures, or the use of excessive toxic reagents. Therefore, the lack of known methods in terms of substrate universality and atom economy greatly limits Large-scale production and practical application of such compounds

Method used

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  • A method for preparing α,α-diamidoalkane compounds with n,n'-dialkylamides
  • A method for preparing α,α-diamidoalkane compounds with n,n'-dialkylamides
  • A method for preparing α,α-diamidoalkane compounds with n,n'-dialkylamides

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preparation example Construction

[0021] The preparation method comprises the following steps:

[0022] S1: Catalyst, substituted amide, liquid N,N'-dialkylamide and sodium trifluoromethanesulfonate (CF 3 SO 2 Na), potassium persulfate (K 2 S 2 o 8 ) were sequentially added to a dry reaction vessel to obtain a mixture.

[0023] S2: heating the mixture obtained in step S1 to react, the reaction temperature is 30-80° C., the reaction time is 1-24 hours, and the α,α-diamidoalkane compound is obtained by separation. The reaction process expression is:

[0024]

[0025] The concentration of the substituted amide in the N,N'-dialkylamide solvent is 0.01-10mol / L. The further recommended concentration is 0.05-2mol / L; especially the recommended concentration is 0.2mol / L;

[0026] The molar ratio of the substituted amide, cuprous bromide, sodium trifluoromethanesulfonate and potassium persulfate is 1:0.01-0.3:0.05-1.5:0.3-9. A further recommended molar ratio of substituted amides, cuprous bromide, sodium trif...

Embodiment 1

[0033] At room temperature, under an air atmosphere, add 0.02mmol cuprous bromide, 0.2mmol substituted amide, 1mL N,N-dimethylformamide (DMF), 0.1mmol sodium trifluoromethanesulfonate and 0.6mmol potassium persulfate, then warming up to 50 ℃ for 16 hours, the reaction process is:

[0034]

[0035] Among them, R 2 is phenyl, R 3 for H. The product was separated by column chromatography:

[0036] N-(N-methylformamido)-methylbenzamide:

[0037]

[0038] White solid with a melting point of 70-72°C and a yield of 96%. The test results are as follows:

[0039] 1 H-NMR (500.1MHz, CDCl3) δ=[8.27(s,0.49H),8.01(s.0.49H)],7.81(d,J=8.0Hz,2H),[7.71(t,J=5.0Hz) ,0.47H),7.56(t,J=5.0Hz,0.47H)],7.53-7.47(m,1H),7.45-7.38(m,2H),[4.95(d,J=7.0Hz,1.03H) ,4.91(d,J=6.0Hz,1.04H)],[3.10(s,1.53H),2.89(s,1.50H)]. 13 C-NMR (125.8MHz, CDCl3) δ = 168.2, 168.0, 163.7, 163.5, 133.31, 133.28, 132.1, 132.0, 128.59, 128.58, 127.2, 127.1, 54.4, 49.1, 34.8, 28.8. HR-MS (ESI) calcd for C 10 h 13 N 2 ...

Embodiment 2

[0041] At room temperature, under an air atmosphere, add 0.02mmol cuprous bromide, 0.2mmol substituted amide, 1mL N,N-dimethylformamide (DMF), 0.1mmol sodium trifluoromethanesulfonate and 0.6mmol potassium persulfate, then warming up to 50 ℃ for 16 hours, the reaction process is:

[0042]

[0043] Among them, R 2 is ethoxyphenyl, R 3 for H. The product was separated by column chromatography:

[0044] N-(N-methylformamido)methyl-o-ethoxybenzamide.

[0045]

[0046] White solid with a melting point of 74-75°C and a yield of 90%. The test results are as follows:

[0047] 1 H-NMR (500.1MHz, CDCl3)δ=[8.80-8.67(br,0.46H),8.53-8.40(br,0.50H)],[8.33(s,0.53H),8.04(s,0.48H)] ,8.15(t,J=7.8Hz,1H),7.47-7.38(m,1H),7.10-7.00(m,1H),6.94(t,J=7.8Hz,1H),[4.96(d,J= 6.5Hz, 1.00H), 4.91(d, J=6.5Hz, 1.09H)], 4.24-4.11(m, 2H), [3.10(s, 1.51H), 2.92(s, 1.56H)], 1.55- 1.42(m,3H). 13 C-NMR (125.8MHz, CDCl3) δ = 166.2, 166.0, 163.5, 163.1, 157.2, 156.9, 133.4, 133.2, 132.3, 132.2, 121.4, 1...

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Abstract

The invention provides a method for preparing α,α-diamidoalkane compounds from N,N'-dialkylamides, comprising the following steps: S1, adding catalyst, substituted amide, N,N'-dialkyl The amide, sodium triflate, and potassium persulfate were sequentially added to a dry reaction vessel to obtain a mixture. S2. Raising the temperature of the mixture obtained in step S1 to react, the reaction temperature is 30-80° C., and the reaction time is 1-24 hours, and the α,α-diamidoalkane compound is obtained by separation. The method has wide sources of raw materials, convenient and safe operation, and has broad application value in the field of chemical synthesis.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a method for preparing α,α-diamidoalkane compounds from N,N'-dialkylamides. Background technique [0002] N,N'-dialkylamide compounds such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC) and N-methylpyrrolidone (NMP) are common chemical raw material. It has a wide range of uses and is an excellent organic solvent and an important organic synthesis intermediate. Since these compounds belong to relatively cheap bulk chemicals, it will be an economical and efficient method to synthesize high-value functional group compounds, such as the direct amidation reaction of C-H bonds, from these cheap and easy-to-obtain N-alkylamide compounds. Chemical finishing methods. [0003] However, the currently disclosed C-H functional group methods for N-alkylamide compounds mainly involve the modification of the C-H bond of the aldehyde group or the C-H bond at the α-position of the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/78C07C231/12C07C235/50C07D213/81C07D333/38C07C233/40C07C311/18C07C303/40C07C239/20C07D307/68C07D207/273
CPCC07C233/78C07C235/50C07D213/81C07D333/38C07C233/40C07C311/18C07C239/20C07D307/68C07D207/273
Inventor 夏远志陈佳佳陈建辉况锦强
Owner WENZHOU UNIV