Method for preparing 2-aryl malonamide and application thereof
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An arylmalonamide and aryl technology, which is applied in the field of preparation of 2-arylmalonamide, can solve the problems of three-waste pollution, high cost, halogen corrosion and the like, and achieves the effects of high yield and low cost
Active Publication Date: 2018-10-23
ORIENTAL LUZHOU AGROCHEM
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In the process of diazotization-halogenation reaction, not only a large amount of three waste pollution is produced, but also there are safety hazards and halogencorrosion problems
In addition, the C-C metal-catalyzed coupling reaction of the resulting sterically hindered aryl halides with malonic acid derivatives requires the use of expensive organometallic catalysts, which are costly and difficult to recycle
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Embodiment 1
[0017] Example 1: Preparation of 2-(2,6-diethyl-4-methylphenyl) malonamide
[0018] The raw material 2-(2,6-diethyl-4-methyl-2-en-1-cyclohexylene) malononitrile 43.0g (0.20mol), potassiumpersulfate 54.1g (0.2mol) and water 5.4 g (0.30 mol) was cooled to 0-5°C. Concentrated sulfuric acid was added dropwise to the reaction system. After dropping, the temperature was raised to 70°C for reaction. After the reaction is complete, lower the temperature, pour the reaction solution into ice water, extract twice with ethyl acetate, combine the organic phases, dry, concentrate and crystallize to obtain 2-(2,6-diethyl-4-methylphenyl) propaneAmide 40.0g, yield 80%. 1 H NMR (MeOD, 500MHz): δ6.99(s, 2H), 4.81(s, 1H), 2.60(q, J=9.0Hz, 4H), 2.32(s, 3H), 1.22(t, J=9.0 Hz, 6H). 13 C NMR (CDCl 3 ,125MHz): δ174.7, 145.0, 139.0, 130.2, 128.9, 48.9, 27.5, 21.2, 15.5.
Embodiment 2
[0019] Example 2: Preparation of 2-(2,6-diethyl-4-methylphenyl) malonamide
[0020] The raw material 2-(2,6-diethyl-4-methyl-2-en-1-cyclohexylene) malononitrile 21.4g (0.10mol), 30% hydrogenperoxide 13.6g (0.12mol) were cooled to 0 -5°C. After dropping, the temperature was raised to 60°C for reaction. After the reaction is complete, lower the temperature, pour the reaction solution into ice water, extract twice with ethyl acetate, combine the organic phases, dry, concentrate and crystallize to obtain 2-(2,6-diethyl-4-methylphenyl) propaneAmide 10.2 g.
Embodiment 3
[0021] Example 3: Preparation of 2-(2,6-diethyl-4-methylphenyl) malonamide
[0022] Cool the raw material 2-(2,6-diethyl-4-methyl-2-en-1-cyclohexylene) malononitrile 32.1g (0.15mol), water 6.7g (0.30mol) to 0-5 ℃. Concentrated sulfuric acid was added dropwise to the reaction system. After dropping, the temperature was raised to 80°C for reaction. After the reaction is complete, lower the temperature, pour the reaction solution into ice water, extract twice with ethyl acetate, combine the organic phases, dry, concentrate and crystallize to obtain 2-(2,6-diethyl-4-methylphenyl) propaneAmide 32.7g, yield 88%.
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Abstract
The invention provides a method for preparing 2-aryl malonamide and application thereof. According to the method, 2-(cyclohexadienylidene)malononitrile is used as a raw material and undergoes an aromatization-hydrolysis reaction under the action of an oxidizing agent and water so as to obtain 2-arylmalonamide in one step. Compared with the prior art, the method for preparing 2-arylmalonamide provided by the invention has the following remarkable features and advantages: (1) completely different synthesis strategies are adopted; (2) the raw material is simple and easily available; and (3) yieldis high, the use of expensive metal catalysts is avoided, cost is low, and the method is suitable for industrial production.
Description
technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method and application of 2-aryl malonamide. Background technique [0002] 2-Arylmalonamide compounds are an important class of intermediates in organic synthesis. For example, 2-(2,6-diethyl-4-methylphenyl)malonamide is an important intermediate for the preparation of the highly effective herbicide pinoxaden (WO000 / 78881, WO 00 / 78712). [0003] The current method for synthesizing 2-aryl malonamide compounds is mainly to prepare by hydrolysis of 2-aryl malononitrile compounds (WO 00 / 78712). This method has the problem that the raw material 2-aryl malononitrile compound is difficult to prepare, especially the preparation of the 2-(2,6-disubstituted aryl) malononitrile raw material with large steric hindrance. The best way to synthesize 2-(2,6-disubstituted aryl) malononitriles is to use the corresponding aromatic amine compounds as raw materials, follow...
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