Benzyl thioether compound and preparation method thereof

A technology for benzylic thioethers and compounds, which is applied in the field of benzylic thioethers and their preparations, can solve the problems of strong irritation and toxicity of mercaptans, high cost, etc., and achieve high yield, simple raw materials, and mild reaction conditions Effect

Pending Publication Date: 2022-03-15
苏州照固新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the preparation methods disclosed in the above documents, transition metal palladium needs to be used as a catalyst, which is expensive, and the raw materials of halogenated hydrocarbons are limited, mercaptans are highly irritating and toxic, and the reaction requires harsh reaction conditions such as strong oxidants and higher temperatures.

Method used

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  • Benzyl thioether compound and preparation method thereof
  • Benzyl thioether compound and preparation method thereof
  • Benzyl thioether compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A kind of benzylic sulfide compound (naphthalene-2-ylmethyl) (phenyl) sulfide and preparation method thereof, the specific steps are as follows:

[0035]

[0036] In the glove box, an oven-dried screw cap 8 mL vial equipped with a magnetic stir bar was charged with methyl (naphthalen-2-ylmethyl)oxalate (0.2 mmol), thiosulfonate (0.24 mmol) and NiBr via syringe 2 (5.0 mol%), ligand 1,10-phenanthroline (10 mol%), Mn (1.5 equiv.), DMSO (1 mL), and the mixture was stirred at 40° C. for 24 h. After 24 h, the crude reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (20 mL x 3). Na for organic layer 2 SO 4 Dry, filter and concentrate. The residue was purified by flash chromatography to give the product in 69% yield.

[0037] The compound prepared in this embodiment is detected, and the detection results are as follows:

[0038] Infrared spectrum (neat, ν, cm-1): 2953, 2921, 2852, 1730, 1477, 1438, 1270, 1089, 1022, 776, 686, 453, 470;

[003...

Embodiment 2

[0043]A benzylic sulfide compound ((6-methoxynaphthalene-2-yl) methyl) (phenyl) sulfide and a preparation method thereof, the specific steps are as follows:

[0044]

[0045] In a glove box, an oven-dried screw cap 8 mL vial equipped with a magnetic stir bar was charged with methyl (6-methoxynaphthalen-2-yl)methyl oxalate (0.2 mmol), thiosulfonate (0.24 mmol ) by adding NiBr via syringe 2 (5.0 mol%), ligand 1,10-phenanthroline (10 mol%), Mn (1.5 equiv.), DMSO (1 mL), and the mixture was stirred at 40° C. for 24 h. After 24 h, the crude reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (20 mL x 3). Na for organic layer 2 SO 4 Dry, filter and concentrate. The residue was purified by flash chromatography to give the product in 67% yield.

[0046] The compound prepared in this embodiment is detected, and the detection results are as follows:

[0047] Infrared spectrum (neat, ν, cm-1): 2920, 2850, 2361, 1599, 1435, 1261, 1163, 1024, 856, 814, 73...

Embodiment 3

[0052] A kind of benzylic sulfide compound 8-((phenylthio) methyl) quinoline and preparation method thereof, the specific steps are as follows:

[0053]

[0054] In a glove box, an oven-dried screw cap 8 mL vial equipped with a magnetic stir bar was charged with methyl(quinolin-8-ylmethyl)oxalate (0.2 mmol), thiosulfonate (0.24 mmol) by Syringe added NiBr 2 (5.0 mol%), ligand 1,10-phenanthroline (10 mol%), Mn (1.5 equiv.), DMSO (1 mL), and the mixture was stirred at 40° C. for 24 h. After 24 h, the crude reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (20 mL x 3). Na for organic layer 2 SO 4 Dry, filter and concentrate. The residue was purified by flash chromatography to give the product in 63% yield.

[0055] The compound prepared in this embodiment is detected, and the detection results are as follows:

[0056] Infrared spectrum (neat, ν, cm-1): 2921, 2853, 1725, 1573, 1472, 1272, 1071, 793, 728, 688;

[0057] Proton NMR spectrum (400M...

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Abstract

The invention relates to a benzyl thioether compound and a preparation method thereof, and belongs to the technical field of organic compounds. The preparation method provided by the invention comprises the following step: in a protective atmosphere, oxalate and a sulfur source react in a solvent under the action of a catalyst, a reducing agent and a ligand to obtain the benzyl thioether compound. According to the preparation process of the benzyl thioether compound, oxalate and a sulfur source are used as raw materials, the raw materials are simple and easy to obtain, the reaction condition is mild and environment-friendly, nickel halide is used as a catalyst in the reaction, the obtained yield is high, and the method can be suitable for amplification reaction and lays a foundation for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic compounds, in particular to a benzylic sulfide compound and a preparation method thereof. Background technique [0002] Sulfur-containing organic compounds widely exist in the body of animals and plants. They are important components of biologically active molecules and natural products such as proteins, amino acids, and vitamins, and play an important role in maintaining the metabolism and life activities of organisms. Due to its special structural properties, it is widely used in pesticides, medicines, materials and other fields. Thioether is an important component of sulfur-containing compounds. In recent years, chemists have been continuously developing effective methods for preparing multifunctional thioether compounds. [0003] The thioether skeleton widely exists in natural products and drug molecules, and the representative structural formula is as follows: [0004] [0005] The tradi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07D213/32C07D215/12C07B45/06C07C321/28C07C323/16C07C323/07
CPCC07C319/14C07D213/32C07D215/12C07B45/06C07B2200/07C07C321/28C07C323/16C07C323/07
Inventor 汪顺义宋萍陈莹赵固
Owner 苏州照固新材料科技有限公司
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