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A kind of n-hydrocarbylthio-n-allyl substituted amides compound and its preparation method

A technology of amide compounds and allyl substitution, which is applied in organic chemistry and other fields, and can solve problems such as poor tolerance and restrictions of functional groups

Active Publication Date: 2021-08-20
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of oxidizing agents makes the functional group tolerance of the reaction poor, which is limited in the synthesis of complex molecules

Method used

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  • A kind of n-hydrocarbylthio-n-allyl substituted amides compound and its preparation method
  • A kind of n-hydrocarbylthio-n-allyl substituted amides compound and its preparation method
  • A kind of n-hydrocarbylthio-n-allyl substituted amides compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of N-thiol-N-allyl substituted amides by reacting N-t-pentanoyloxyaryl formamide with allyl phenylene sulfide

[0036]

[0037] At room temperature, under an air atmosphere, in a dry reaction test tube, add N-tert-valeryloxyarylcarboxamide (0.2mmol), allylphenyl sulfide (0.26mmol), RuCl 2 (PPh 3 ) 3 (0.01mmol), benzohydroxamic acid (0.02mmol), silver acetate (AgOAc) (0.04mmol) and methanol (1mL), followed by stirring at room temperature for 10 minutes, after the reaction was completed, the product was separated by column chromatography. The product is a white solid with a yield of 96%, and the detection results are as follows:

[0038]

[0039] 1 H NMR (400MHz, CDCl 3 )δ: 7.42(d, J=7.0Hz, 2H), 7.32(t, J=7.4Hz, 1H), 7.29–7.21(m, 4H), 7.14(t, J=7.4Hz, 1H), 7.04( d,J=7.6Hz,2H),5.89(ddt,J=16.0,9.9,6.1Hz,1H),5.20(d,J=4.0Hz,1H),5.16(s,1H),4.28(d,J =5.9Hz,2H). 13 C NMR (125MHz, CDCl 3 )δ: 176.02, 137.82, 135.32, 132.85, 130.37, 129.38, 127.95, 127.56, 1...

Embodiment 2

[0041] Synthesis of N-hydrocarbylthio-N-allyl substituted amides by reaction of N-tert-valeryloxy-p-chlorobenzamide and allylphenylene sulfide

[0042] At room temperature, under an air atmosphere, add N-tert-valeryloxy-p-chlorobenzamide (1 mmol), allyl phenylene sulfide (0.5 mmol), RuCl 2 (PPh 3 ) 3 (0.01mmol), benzohydroxamic acid (0.001mmol), silver acetate (AgOAc) (0.04mmol) and methanol (1mL), followed by stirring at room temperature for 10 minutes, after the reaction was completed, the product was separated by column chromatography. The product is a white solid with a yield of 82%, and the detection results are as follows:

[0043]

[0044] 1 H NMR (400MHz, CDCl 3 )δ: 7.37(d, J=8.6Hz, 2H), 7.26(t, J=7.7Hz, 2H), 7.22(d, J=8.6Hz, 2H), 7.15(t, J=7.4Hz, 1H) , 7.02 (d, J=7.5Hz, 2H), 5.94–5.82 (m, 1H), 5.23–5.11 (m, 2H), 4.27 (d, J=6.0Hz, 2H).13C NMR (125MHz, CDCl 3 )δ: 175.02, 137.60, 136.53, 133.63, 132.64, 129.50, 129.15, 128.24, 127.18, 124.42, 118.77, 54.48.

Embodiment 3

[0046] Synthesis of N-hydrocarbylthio-N-allyl substituted amides by reaction of N-tert-valeryloxy-p-chlorobenzamide and allylphenylene sulfide

[0047] At room temperature, under air atmosphere, in a dry reaction test tube, add N-tert-valeryloxy-p-chlorobenzamide (1 mmol), allyl phenylene sulfide (0.8 mmol), RuCl 2 (PPh 3 ) 3 (0.1mmol), benzohydroxamic acid (0.1mmol), silver acetate (AgOAc) (0.2mmol) and methanol (5mL), followed by stirring the reaction at 25°C for 10 minutes under solvent-free conditions,

[0048] After the reaction, the product was separated by column chromatography. The product is a white solid with a yield of 94%, and the detection results are as follows:

[0049]

[0050] 1 H NMR (400MHz, CDCl 3 )δ: 7.38(d, J=8.5Hz, 6H), 7.29(d, J=8.6Hz, 7H), 7.25(d, J=7.8Hz, 5H), 7.14(t, J=7.4Hz, 3H) ,7.01(d,J=7.6Hz,6H),5.99–5.73(m,3H),5.18(dd,J=13.5,2.1Hz,6H),4.27(d,J=5.9Hz,6H). 13 C NMR (125MHz, CDCl 3 )δ: 175.10, 137.57, 134.12, 132.61, 131.20, 129.51, 129....

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Abstract

The invention discloses an N-hydrocarbylthio-N-allyl substituted amide compound and a preparation method thereof. The raw materials are N-hydrocarbon acyloxyamide and allyl hydrocarbon sulfide, and RuCl 2 (PPh 3 ) 3 The complex is a catalyst, and it is prepared by reacting in an organic solvent or without a solvent under an air atmosphere in the presence of benzohydroxamic acid and silver acetate. The invention has mild reaction conditions, wide substrate application range, simple and convenient operation, and the product is an N-hydrocarbyl thio-substituted amide compound, which has very good derivatization application potential.

Description

technical field [0001] The invention relates to the technical field of metal catalytic synthesis, in particular to an N-hydrocarbylthio-N-allyl substituted amide compound and a preparation method thereof. Background technique [0002] Nitrogen-sulfur (N-S) bonds have unique functional groups and biological activities, and are widely found in natural products. Compound molecules containing N-S bonds have important applications in the fields of drug synthesis, synthetic rubber, dyes, and lubricating oils[a)J .Nat.Prod.2018,81,423; b) Med.Res.Rev.2006,26,767; c) Chem.Rev.1989,89,689; d) Sulfur-Nitrogen Compounds: Compounds with Sulfur of Oxidation Number II, 8thed.; Springer - Verlag: Berlin, Heidelberg, 1994; pp XXIV, 325.]. Therefore, the construction of N-S is one of the research hotspots of synthetic chemists. The current synthetic strategy generally adopts oxidative reaction conditions, and uses iodine or copper catalyst / oxygen to realize the construction of N-S bond [a] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C313/28C07D307/68
CPCC07C313/28C07D307/68C07C2601/14
Inventor 夏远志林波陈建辉
Owner WENZHOU UNIV