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Preparation method of N-acetyl tellurium carbamate compound

A technology of carbamates and carbamates, applied in the field of drug preparation, to achieve the effects of high yield, easy availability of raw materials, and convenient operation

Active Publication Date: 2022-01-11
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This patent aims to synthesize a special class of telluride carbamate compounds substituted by N-acetyl groups. This is a novel structure, and there has been no corresponding report before.

Method used

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  • Preparation method of N-acetyl tellurium carbamate compound
  • Preparation method of N-acetyl tellurium carbamate compound
  • Preparation method of N-acetyl tellurium carbamate compound

Examples

Experimental program
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Embodiment 1

[0036] In this embodiment, a tellurium-(4-methylphenyl)-N-acetyl-N-(2,6-dimethylphenyl)telluride carbamate has the following structural formula:

[0037]

[0038] A method for preparing the compound of this embodiment, using the following steps:

[0039] Under air atmosphere, add 26.2 mg of 2,6-dimethylbenzeneisonitrile and 131.4 mg of di-4-tolyl ditelluride and 161 mg of trihydrate and manganese acetate into a 25 ml reaction flask, then add 2.0 ml of acetonitrile , heated to 100°C, and reacted for 12h. After cooling, filter through celite and elute with dichloromethane. Pour into 10 ml of water, extract the product with 30 ml of dichloromethane, wash with saturated brine, dry over anhydrous sodium sulfate, and remove the solvent with a rotary evaporator to obtain a crude product; the crude product is subjected to column chromatography (PE:EA=30: 1) Purification to obtain 61 mg of product with a yield of 74%. Melting point: 101-103°C.

[0040]The characterization data o...

Embodiment 2

[0042] This embodiment is basically the same as Embodiment 1, especially in that:

[0043] In this example, a tellurium-(p-methylphenyl)-N-acetyl-N-(4-methyl-[1,1'-biphenyl]-2-yl)tellurinomethyl Ester, its structural formula is as follows:

[0044]

[0045] A method for preparing the compound of this embodiment, the specific steps are as follows:

[0046] Under air atmosphere, add 58.3 mg of 2-isocyano-5-methyl-1,1'-biphenyl and 196.9 mg of di-4-tolyl ditelluride and 241.3 mg of trihydrate into a 25 mL reaction tube And manganese acetate, and then add 2.0 ml of acetonitrile, heated to 80 ° C, the reaction 12h. After cooling, filter through celite and elute with dichloromethane. Pour into 10 ml of water, extract the product with 30 ml of dichloromethane, wash with saturated brine, dry over anhydrous sodium sulfate, and remove the solvent with a rotary evaporator to obtain a crude product; the crude product was purified by column chromatography (PE:EA=20:1 ) purification ...

Embodiment 3

[0049] This embodiment is basically the same as the previous embodiment, and the special features are:

[0050] In this embodiment, a tellurium-(p-tolyl)-N-acetyl-N-(2-chlorophenyl)telluride carbamate has the following structural formula:

[0051]

[0052] A method for preparing the compound of this embodiment, the specific steps are as follows:

[0053] Under an air atmosphere, add 41.3 mg of 2-chlorophenylisonitrile and 196.9 mg of di-4-tolyl ditelluride and 241.3 mg of trihydrate and manganese acetate in a 25 ml reaction tube, then add 2.0 ml of acetonitrile and heat To 60°C, react for 12h. After cooling, filter with celite and elute with dichloromethane. Pour into 10 ml of water, extract the product with 30 ml of dichloromethane, wash with saturated brine, dry over anhydrous sodium sulfate, and remove the solvent with a rotary evaporator to obtain a crude product; the crude product was purified by column chromatography (PE:EA=20:1 ) was purified to obtain 83 mg of wh...

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Abstract

The invention discloses a preparation method of an N-acetyl tellurium carbamate compound, wherein the structural formula of the compound is shown in the specification, and in the formula, R1 is alkyl, aryl or heterocyclic aryl, and R2 is alkyl, aryl or heterocyclic aryl. According to the invention, simple and easily available isonitrile (R1NC) and symmetric ditelluride (R2TeTeR2) are used as raw materials, and the N-acetyl tellurium carbamate compound is efficiently synthesized in the presence of acetate; the method has the advantages of mild reaction conditions, simple operation, high yield and the like, and is especially suitable for introducing an N-acetyl tellurium carbamate structure into a complex molecular skeleton; and the method can be widely applied to the fields of medicine molecules, materials and the like.

Description

technical field [0001] The invention relates to an N-acetyl telluride carbamate compound and a preparation method thereof, which are applied in the technical field of medicine preparation. Background technique [0002] In the past three decades, organotellurium chemistry has received the attention of the scientific community. As a member of the chalcogenides, tellurium has been gradually applied in organic synthesis, medicinal chemistry, biochemistry, materials science and other fields (Chem.Sci., 2019, 10, 7068-7075). Recently, because of the interesting reactivity and potential biological activity of tellurium-containing compounds (Chem. Rev., 2004, 104, 6255-6285; Org. Biomol. Chem., 2010, 8, 4203-4216), the study of tellurium-containing compounds has received more and more attention. [0003] Carbamates, thiocarbamates and selenocarbamates are important intermediates in organic synthesis and exhibit good biological activities. Many drug molecules contain carbamate and...

Claims

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Application Information

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IPC IPC(8): C07C395/00
CPCC07C395/00C07C2601/14Y02P20/55
Inventor 谭启涛査健健曲裕辉许斌刘秉新
Owner SHANGHAI UNIV