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Preparation method of benzisothiazole derivatives

A technology for benzisothiazole derivatives and derivatives, which is applied in the field of preparation of benzisothiazole derivatives, can solve the problems that benzisothiazole derivatives have not been reported, and achieve various types, high yields, and easy operation. simple effect

Inactive Publication Date: 2017-11-07
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, an efficient and facile method for synthesizing benzisothiazole derivatives has not been reported

Method used

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  • Preparation method of benzisothiazole derivatives
  • Preparation method of benzisothiazole derivatives
  • Preparation method of benzisothiazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Methyl phenyl sulfide (I) (496mg, 4mmol), N, N, N', N'-tetramethylethylenediamine (TMEDA, II) (1.86g, 16mmol), n-BuLi (16mmol) Add n-hexane solution (concentration of n-BuLi(III) n-hexane solution is 1.0M) to anhydrous n-hexane (10mL) successively under nitrogen protection, react at 70°C for 2 hours, cool, filter and dry , to give white powder (lithiummethyl)(2-lithiumphenyl)sulfide (1.36 g, yield = 70%)

[0021] With 1.2M lithium methoxide n-hexane solution, 2.5M n-C 10 h 23 Li n-hexane solution replaces the n-BuLi n-hexane solution of the present embodiment respectively, its lithium methylate or n-C 10 h 23 Li all use 16mmol, other is the same as this embodiment, the white powder (lithium methyl) (2-lithium phenyl) sulfide that prepares, its yield is respectively 69.2% and 71.5%.

[0022] The nitrogen in this example was replaced by helium, and the others were the same as in this example to prepare white powdery (lithium methyl)(2-lithium phenyl) sulfide.

[0023...

Embodiment 2

[0026] Preparation of 3-phenylbenzisothiazole (VI-a):

[0027]

[0028] Add (lithiummethyl)(2-lithiumphenyl)sulfide (96.8mg, 0.2mmol) and benzonitrile (V-a) (82.4mg, 0.8mmol) to the n-hexane solution successively, and react at room temperature for 24h. After the reaction was completed, 5 mL of saturated ammonium chloride solution was added, extracted with dichloromethane (5 mL*3), dried, concentrated, and separated by column to obtain 3-phenylbenzisothiazole (VI-a), a white solid (38.8 mg, 92%). 1 H NMR (400MHz, CDCl 3 )δ8.19(d,J=8.2Hz,1H),8.00(d,J=8.2Hz,1H),7.93–7.84(m,2H),7.63–7.50(m,4H),7.47(dd,J =8.1,1.0Hz,1H). 13 C NMR (101MHz, CDCl 3 )δ164.40, 153.52, 135.23, 133.82, 129.35, 128.83, 128.72, 127.51, 125.02, 124.86, 119.96.

Embodiment 3

[0030] Preparation of 3-(2-methylphenyl)benzisothiazole (VI-b):

[0031]

[0032] (Lithium methyl) (2-lithium phenyl) sulfide (96.8mg, 0.2mmol), 2-methylbenzonitrile (V-b) (93.6mg, 0.8mmol) were successively added to the n-hexane solution, and the mixture was heated at room temperature Under the condition of reaction 24h. After the reaction was completed, 5 mL of saturated ammonium chloride solution was added, extracted with dichloromethane (5 mL*3), dried, concentrated, and separated by column to obtain 3-(2-methylphenyl)benzisothiazole (VI-b ), white solid (30.2 mg, 67%). 1 H NMR (400MHz, CDCl 3 )δ8.00(d,J=8.2Hz,1H),7.76(d,J=8.2Hz,1H),7.55(ddd,J=8.1,7.0,1.0Hz,1H),7.48–7.28(m,5H ),2.27(s,3H). 13 CNMR (101MHz, CDCl 3 )δ165.27, 152.57, 137.29, 135.11, 134.35, 130.79, 129.69, 129.04, 127.50, 125.67, 124.89, 124.78, 119.73, 20.03.

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Abstract

The invention discloses a preparation method of a benzisothiazole derivative. The method comprises the following steps that a benzyl disulfide (I), N,N,N',N'-tetramethylethylenediamine (II) and a C1-C10 lithium alkylide (III) normal hexane solution are sequentially added into a solvent, reaction, filtering and drying are performed to obtain di-lithium compound white powder, the di-lithium compound and a cyano compound (V) are subjected to a reaction under the room temperature, and the benzisothiazole derivative (VI) is obtained. The method has the advantages that operation is easy, reaction raw materials and reaction reagents are easy to obtain, product substituent groups have diversified types, and the yield is high.

Description

technical field [0001] The invention relates to a preparation method of benzisothiazole derivatives. Background technique [0002] Benzisothiazole derivatives are an important class of heterocyclic molecules. In recent years, since this type of heterocyclic skeleton has been found to have special biological activities such as inhibiting nerve excitation and chymotrypsin inhibitor, the research on the construction of this type of heterocyclic skeleton has attracted more and more attention from chemical synthesis workers. In the previous synthesis of this type of molecule, due to the existence of an uncommon chemical bond such as the N-S bond, the synthesis of this type of molecule is extremely challenging. In 2000, the McNab group reported that at 650°C, the vacuum pressure was 10 -2 -10 -3 Under the extreme conditions of Torr, the synthesis of benzisothiazole molecules was realized. [0003] [1] J.M.Singer, B.M.Barr, L.L.Coughenour, T.F.Gregory, M.A.Walters, Bioorg.Med.C...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D275/04
CPCC07D275/04
Inventor 黄剑辉陈捷熊潇瑜朱冉冉王云涛
Owner TIANJIN UNIV