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Preparation method of sulfonyl acetonitrile compound

A technology of sulfonylacetonitrile and compounds, which is applied in the preparation of organic compounds, chemical instruments and methods, and preparation of sulfides, can solve problems such as harsh reaction conditions, and achieve good guiding significance and application prospects

Active Publication Date: 2020-08-11
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional method of synthesizing sulfonylacetonitrile compounds requires the use of irritating and toxic sulfuryl chloride or sulfonic acid, the reaction conditions are harsh, and additional metal catalysts or oxidants are required

Method used

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  • Preparation method of sulfonyl acetonitrile compound
  • Preparation method of sulfonyl acetonitrile compound
  • Preparation method of sulfonyl acetonitrile compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] At room temperature, p-tolyldiazonium salt (0.2 mmol), sodium metabisulfite (0.4 mmol), 3-azido-2-methylbut-3-en-2-ol ( 0.3mmol), plugged the reaction tube with a stopper and replaced it three times in high-purity nitrogen or argon, so that the system was in anaerobic condition, then added 1,2-dichloroethane (2mL), and stirred at room temperature until TLC Monitor until complete reaction. The reaction liquid was directly concentrated under reduced pressure, and the mixed system of petroleum ether and ethyl acetate was used as the mobile phase for column chromatography separation to obtain the corresponding sulfonylacetonitrile compound Example 1.

[0022] Structural characterization of compound example 1: 1 H NMR (400MHz, CDCl 3 )δ (ppm) 7.89 (d, J = 7.7Hz, 2H), 7.43 (d, J = 7.8Hz, 2H), 4.02 (s, 2H), 2.48 (s, 3H); 13 C NMR (100MHz, CDCl 3 )δ147.1, 133.9, 130.7, 129.1, 110.7, 46.1, 22.0.

Embodiment 2

[0024]

[0025] At room temperature, add p-methoxyphenyl diazonium salt (0.2 mmol), sodium metabisulfite (0.4 mmol), 3-azido-2-methylbut-3-ene-2- Alcohol (0.3mmol), plug the reaction tube with a stopper and place it in high-purity nitrogen or argon for three times, so that the system is in anaerobic condition, add 1,2-dichloroethane (2mL), and stir at room temperature Until the complete reaction was monitored by TLC. The reaction solution was directly concentrated under reduced pressure, and the mixed system of petroleum ether and ethyl acetate was used as the mobile phase for column chromatography separation to obtain the corresponding sulfonylacetonitrile compound Example 2.

[0026] Structural characterization of compound example 2: 1 H NMR (400MHz, CDCl 3 )δ8.00-7.92(m,2H),7.14-7.05(m,2H), 4.03(s,2H),3.93(s,3H); 13 C NMR (100MHz, CDCl 3 )δ165.1, 131.3, 128.0, 115.0, 110.8, 55.9, 46.0.

Embodiment 3

[0028]

[0029]At room temperature, add p-methylthiophenyl diazonium salt (0.2 mmol), sodium metabisulfite (0.4 mmol), 3-azido-2-methylbut-3-ene-2- Alcohol (0.3mmol), plug the reaction tube with a stopper and place it in high-purity nitrogen or argon for three times, so that the system is in anaerobic condition, add 1,2-dichloroethane (2mL), and stir at room temperature Until the complete reaction was monitored by TLC. The reaction solution was directly concentrated under reduced pressure, and the mixed system of petroleum ether and ethyl acetate was used as the mobile phase for column chromatography separation to obtain the corresponding sulfonylacetonitrile compound Example 3.

[0030] Structural characterization of compound example 3: 1 H NMR (400MHz, CDCl 3 )δ7.93-7.85(m,2H),7.44-7.38(m,2H), 4.04(s,2H),2.56(s,3H); 13 C NMR (100MHz, CDCl 3 )δ150.1, 131.8, 129.1, 125.5, 110.6, 45.9, 14.6.

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Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of sulfonyl acetonitrile compounds. The structure of the compound is characterized by 1H NMR, 13C NMR and other methods and is confirmed. The method comprises the following steps: taking 2, 2-dichloroethane as a solvent and aryl diazonium salt and sodium pyrosulfite (Na2S2O5) as a catalyst without metal catalyst, generating aryl sulfonyl free radicals on site at room temperature, carrying out free radical addition reaction on 3-azido-2-methylbutyl-3-ene-2-ol, and removing monomolecular nitrogen and 2-hydroxypropyl free radicals to obtain the sulfonyl acetonitrile compound. The preparation method of the sulfonyl acetonitrile compound has the advantages of being mild in condition, simple, efficient, high in reaction yield, wide in substrate application range, good in product purity, convenient to separate and purify and good in application value.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of sulfonylacetonitrile compounds Background technique [0002] Sulfonylacetonitrile compounds are an important class of intermediates in organic synthesis and pharmaceutical synthesis, and play an important role in the fields of organic and medicinal chemistry. For example, arylsulfonyl acetonitrile compounds can react with imines to synthesize β-aminonitriles, which are used in the preparation of various pesticides, food, medicine, and feed additives. [(a) G.C. Tsui, Q. Glenadel, C. Lau, M. Lautens, Org. Lett., 2011, 13, 208; (b) S. Diosdado, R. López, C. Palomo, Chem. Eur. J. 2014 ,20,6526.] In addition, triazolothienopyrimidine UT-B inhibitors can selectively and reversibly inhibit urea transport and reduce urine concentration in urine (M.O. Anderson, J. Zhang, Y. Liu, C .Yao, P.-W.Phuan, A.S.Verkman, J.Med.Chem.2012,55,5942); Rv26...

Claims

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Application Information

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IPC IPC(8): C07B45/04C07C315/00C07C317/44C07C319/20C07C323/65
CPCC07B45/04C07C315/00C07C319/20C07C317/44C07C323/65
Inventor 何福生吴劼叶盛青
Owner TAIZHOU UNIV
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