Synthesis method of N-(cyano (2-cyano substituted phenyl) methyl) substituted tertiary amine

A cyano-substituted, tertiary amine technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as cumbersome operation steps and harsh reaction conditions

Pending Publication Date: 2021-11-23
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the existing synthesis literature for this type of compound is to prepare halogenated aromatic hydrocarbons first, and then react with cuprous cyanide to obtain products.

Method used

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  • Synthesis method of N-(cyano (2-cyano substituted phenyl) methyl) substituted tertiary amine
  • Synthesis method of N-(cyano (2-cyano substituted phenyl) methyl) substituted tertiary amine
  • Synthesis method of N-(cyano (2-cyano substituted phenyl) methyl) substituted tertiary amine

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Experimental program
Comparison scheme
Effect test

Embodiment

[0016] 1. Using indolinylamino-malononitrile and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate as raw materials (reaction formula 1)

[0017]

[0018] Under the protection of argon, in a 10mL reaction tube, indolinylamino-malononitrile (100mg, 0.55mmol), 2-(trimethylsilyl)phenyltrifluoromethanesulfonate (244mg, 0.82 mmol), cesium fluoride (165mg, 1.09mmol) and 18-crown-6 (289mg, 1.09mmol), were sequentially added to stirred tetrahydrofuran (2mL), reacted at 30°C for 2 hours to complete the reaction, and The solvent was sucked dry on the instrument, and a white solid (106 mg, 75% yield) was obtained by column chromatography.

[0019] The product detection data are as follows:

[0020] 1 H NMR (400MHz, CDCl 3 )δ7.91(d, J=7.6Hz, 1H), 7.79(d, J=7.6Hz, 1H), 7.73(t, J=7.6Hz, 1H), 7.57(t, J=7.6Hz, 1H) ,7.17(t,J=7.2Hz,2H),6.87(t,J=7.2Hz,1H),6.78(d,J=8.0Hz,1H),5.97(s,1H),3.44-3.37(m, 1H),3.17-3.12(m,1H),3.09-3.02(m,1H),3.00-2.91(m,1H); 13 C NMR (100MHz, CDCl 3 )δ148.29,136.

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of N-(cyano (2-cyano substituted phenyl) methyl) substituted tertiary amine. The reaction general formula is shown in the description. According to the invention, N, N-disubstituted amino-malononitrile and substituted 2-(trimethylsilyl) phenyl trifluoromethane sulfonate are subjected to a substitution reaction under the action of a catalyst to synthesize the N-(cyano (2-cyano substituted phenyl) methyl) substituted tertiary amine compound. The method has the advantages of easily available initial raw materials, simple operation, mild reaction conditions and cheap catalyst, can reduce the input amount of funds and labor force, and provides a rapid and efficient preparation method for the N-(cyano (2-cyano substituted phenyl) methyl) substituted tertiary amine derivative.

Description

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Claims

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Application Information

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Owner LANZHOU UNIVERSITY
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