Allyl sulphide compound and preparation method thereof

A technology of allyl sulfide and compounds, which is applied in the field of allyl sulfide compounds and their preparation, can solve the problems of reduced scope of application of substrates, metal residues in products, unfavorable practical operations, etc., and achieves a simple and efficient synthesis method , short reaction route, less waste

Active Publication Date: 2020-11-20
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the preparation of alkenyl sulfides mainly includes oxidant-assisted free radical addition reaction (Li, C.; Li, J.; Tan, C.; Wu, W.; Jiang, H., Org. Chem. Front ., 2018,5,3158-3162.), nucleophilic substitution reactions of allyl halides with thiophenols and thiols (Herkert, L.; Green, S.L.J.; Barker, G.; Johnson, D.G.; Lee, A .-L., Chem.Eur.J.; 2014,20,11540-11548.), 1,3-diene substrate, hydrosulfurization reaction of alkyne substrate (Yang, X.-H.; Davison, R.T.; Dong, V.M., J.Am. Chem.Soc.; 2018, 140, 10443-10446.), the introduction of sulfur-containing groups directly to the allyl carbon atoms via carbon-hydrogen bond activation (Kim, J .; Kang, B.; Hong, S.H.,.ACS Ca

Method used

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  • Allyl sulphide compound and preparation method thereof
  • Allyl sulphide compound and preparation method thereof
  • Allyl sulphide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Get α-methylstyrene (24mg, 0.2mmol), N-p-tolylthiosuccinimide (53mg, 0.24mmol), pyridine hydrochloride (11mg, 0.1mmol) and join in a 10mL reaction flask, and then Add 2 mL of 1,2-dichloroethane, heat to 60°C, and stir for 12 hours. After the reaction, add 10 mL of ethyl acetate, add 5 mL of water for extraction, dry the organic phase with anhydrous sodium sulfate, and obtain The target compound was 42 mg, and the yield of the target compound was measured to be 88%.

[0036] Such as Figure 1 ~ Figure 2 Shown, the target compound of present embodiment 1 is 2-phenyl-3-(4-methylphenyl) allyl sulfide, and the structural formula of target compound is:

[0037]

[0038] The proton nuclear magnetic resonance spectrum data of target compound are as follows: 1H NMR (600MHz, CDCl3) δ7.47(d, J=7.3Hz, 2H), 7.36(t, J=7.5Hz, 2H), 7.31(t, J=7.2Hz, 1H), 7.26(d, J =7.0Hz, 2H), 7.10(d, J=7.9Hz, 2H), 5.38(s, 1H), 5.13(s, 1H), 3.94(s, 2H), 2.33(s, 3H).

[0039] The carbon nuclear ma...

Embodiment 2

[0041] On the basis of Example 1, the impact of the molar ratio of terminal olefins, N-tolylthiosuccinimide, and pyridine hydrochloride on the yield of the target compound was studied, and the raw materials were weighed according to the data in Table 1, Test according to the method of embodiment 1.

[0042] Table 1

[0043]

[0044] As can be seen from the data in table 1, when N-p-tolylthiosuccinimide consumption is little, substrate α-methylstyrene can not react fully, and when excessive (1.2 times), productive rate improves to some extent, but far When the excess (3 times) is used, the yield will no longer increase. In order to save raw materials, an excess of 1.2 times is selected. Pyridine hydrochloride has the best effect when the catalytic amount (0.5 times) is used, and the amount of 0.2 times is not enough to efficiently catalyze the reaction. When the amount is far excessive (3 times), the reaction yield will no longer increase, and the excess hydrochloric acid m...

Embodiment 3

[0046] Take α-methylstyrene (24mg, 0.2mmol), N-p-chlorophenylthiosuccinimide (58mg, 0.24mmol), and pyridine hydrochloride (11mg, 0.1mmol) into a 10mL reaction flask, Add 2 mL of 1,2-dichloroethane, heat to 60°C, and stir for 12 hours. After the reaction, add 10 mL of ethyl acetate, add 5 mL of water for extraction, dry the organic phase with anhydrous sodium sulfate, and perform column chromatography. 46 mg of the target compound was obtained, and the yield of the target compound was measured to be 90%.

[0047] The target compound of this embodiment is 2-phenyl-3-(4-chlorophenyl) allyl sulfide, and the structural formula of the target compound is:

[0048]

[0049] The proton nuclear magnetic resonance spectrum data of target compound are as follows: 1 H NMR (600MHz, CDCl 3 )δ7.44–7.43(m,2H),7.38–7.34(m,2H),7.32(d,J=7.2Hz,1H),7.24(d,J=0.9Hz,4H), 5.38(s,1H ),5.14(s,1H),3.94(s,2H).

[0050] The carbon nuclear magnetic resonance spectrum data of target compound are as fol...

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Abstract

The invention discloses an allyl sulphide, and a preparation method thereof. The preparation method comprises the following steps: dissolving terminal olefin, N-aryl (alkyl) sulfenyl succinimide and pyridine hydrochloride in an organic solvent, heating while stirring to react for 6-12 hours, after the reaction is finished, extracting, drying, removing the solvent, separating and purifying to obtain the allyl sulphide compound. The synthesis method disclosed by the invention is simple and efficient, mild in reaction condition, good in functional group tolerance, wide in substrate application range, high in yield, good in selectivity, simple to operate, short in reaction route and less in three wastes, can be used for large-scale synthesis, and avoids using a transition metal catalyst and thiol and thiophenol reagents with high toxicity and strong pungent smell.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to an allyl sulfide compound and a preparation method thereof. Background technique [0002] Allyl sulfide is a very important class of sulfur-containing compounds, and has a wide range of applications in the fields of organic synthesis, medicinal chemistry, and materials. For example, allyl sulfide is usually used as a sulfoxide precursor for the synthesis of diene compounds (Julia, M., J. Organomet. Chem., 1979, 181, 17-20.), allyl sulfide compounds Derivatives of olefins can also be used for olefin metathesis reaction and Michael addition reaction acceptors. In the field of materials, sulfur-containing compounds are more widely used, such as sulfur-containing aggregation-induced luminescent materials (Wang, B.-W.; Angew.Chem.Int .Ed., 2020,59,2338-2343.), sulfur-containing polymers, sulfur-containing molecular switches, etc. Therefore, the development of ...

Claims

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Application Information

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IPC IPC(8): C07C321/28C07C323/09C07C323/20C07C323/22C07C321/10C07C321/22C07C319/14
CPCC07C321/28C07C323/09C07C323/20C07C323/22C07C321/10C07C321/22C07C319/14C07C2601/14
Inventor 刘世文
Owner YANCHENG INST OF TECH
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