Crystal form of N,N-diethyl-2-hydroxy-2-phenylacetamide as well as preparation method and application of crystal form

A technology of phenylacetamide and diethyl, which is applied in the preparation of carboxylic acid amide, botany equipment and method, and the preparation of organic compounds, etc., can solve the problems of economy and environmental protection that are not suitable for large-scale production, and achieve the goal of being suitable for carrying and Transport, reduce production costs, and reduce the effects of three wastes

Pending Publication Date: 2020-09-15
北京斯瑞朗文生物科技有限公司
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  • Abstract
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  • Claims
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Problems solved by technology

This solution is not suitable for large-scale production from the perspective of economy and environmental protection

Method used

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  • Crystal form of N,N-diethyl-2-hydroxy-2-phenylacetamide as well as preparation method and application of crystal form
  • Crystal form of N,N-diethyl-2-hydroxy-2-phenylacetamide as well as preparation method and application of crystal form
  • Crystal form of N,N-diethyl-2-hydroxy-2-phenylacetamide as well as preparation method and application of crystal form

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preparation example Construction

[0034] A preparation method of N,N-diethyl-2-hydroxyl-2-phenylacetamide crystal form, using mandelic acid as a raw material, condensation reaction with cyclohexanone, and then aminolysis reaction with diethylamine, Obtaining the crystal form of N,N-diethyl-2-hydroxyl-2-phenylacetamide specifically comprises the following steps:

[0035] (1) Dissolve mandelic acid [formula (II)] in solvent A, and react with cyclohexanone at 20°C to 200°C for 1h to 96h. After the reaction is complete, filter and concentrate to obtain crude product A [formula (III) ]; Wherein the molar ratio of mandelic acid, solvent A and cyclohexanone consumption is 1: (1~8): (1~8);

[0036]

[0037] (2) Add solvent B to the crude product A, stir, crystallize and centrifuge to obtain the pure product A, heat the pure product A and diethylamine at 20°C to 100°C for 1h to 144h, after the reaction is complete, filter Concentrate, wash and dry to obtain the crude product B [formula (I)]; wherein the molar ratio...

Embodiment 1

[0045] Example 1 Preparation of N,N-diethyl-2-hydroxyl-2-phenylacetamide crystal form 1

[0046] At room temperature, add 15kg of formula (II) to a 50L reaction kettle, inhale 18.2kg of toluene and 14.5kg of cyclohexanone under negative pressure, keep the reaction at 150°C for 48 hours, and separate water during the reaction. After the reaction is complete, the reaction is processed. After the reaction solution is hot-filtered to remove insoluble matter, it is concentrated to remove the solvent to obtain the crude product of formula (Ⅲ). Add 50L of n-hexane to stir and crystallize. After 5 hours, a solid is precipitated, and it is centrifuged to dry to obtain the pure product of formula (Ⅲ). 22.2kg with a purity of 98.0%.

[0047] At room temperature, add the above-mentioned pure product of formula (III) and 21 kg of diethylamine to a 50 L reaction kettle respectively, heat at 50° C. for 72 hours, and perform post-treatment after the reaction is complete. After the reaction s...

Embodiment 2

[0049] Example 2 Preparation of N,N-diethyl-2-hydroxyl-2-phenylacetamide crystal form 2

[0050] At room temperature, add 15kg of formula (II) to a 50L reaction kettle, inhale 31.4kg of xylene and 9.7kg of cyclohexanone under negative pressure, keep the temperature at 110°C for 60 hours, and separate water during the reaction. After the reaction was complete, the reaction was processed, and the solvent was concentrated to remove the crude product of formula (Ⅲ). Add 40 L of petroleum ether to stir and crystallize. After 5 hours, a solid precipitated, and was centrifuged to dry to obtain 21 kg of pure product of formula (Ⅲ), with a purity of 97.1%.

[0051] At room temperature, add the above-mentioned pure product of formula (III) and 7.3 kg of diethylamine to a 50 L reaction kettle respectively, and react at 70° C. for 72 hours. After the reaction is complete, the reaction is post-processed. The reaction solution was concentrated to remove the solvent to obtain a residue. To t...

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Abstract

The invention relates to a crystal form of N,N-diethyl-2-hydroxy-2-phenylacetamide as well as preparation method and an application of crystal form. An X-ray powder diffraction pattern of the crystalform is shown in the specification, and has characteristic peak represented by 2theta diffraction angle: 7.526+ / -0.2 DEG, 10.539+ / -0.2 DEG, 13.020+ / -0.2 DEG, 15.221+ / -0.2 DEG, 16.344+ / -0.2 DEG, 17.977+ / -0.2 DEG, 18.567+ / -0.2 DEG, 19.514+ / -0.2 DEG, 21.065+ / -0.2 DEG, 22.661+ / -0.2 DEG, 23.660+ / -0.2 DEG, 25.348+ / -0.2 DEG, 25.886+ / -0.2 DEG, 26.321+ / -0.2 DEG, 27.033+ / -0.2 DEG, 29.309+ / -0.2 DEG, 30.188+ / -0.2 DEG, and 31.193+ / -0.2 DEG; the crystal form is prepared by taking mandelic acid as a raw material, a condensation reaction with cyclohexanone is carried out and then an aminolysis reaction with diethylamine is carried out, and the method has the advantages of few synthesis steps, no pollution of reactants, mild reaction conditions, simplicity in operation, purity up to 99.9% and less generated three wastes, and is suitable for industrial production. The crystal form can also be used for preparing low-alcohol mosquito repellent liquid, and the low-alcohol formula avoids the harm of high-concentration ethanol to the skin and is suitable for children and people with sensitive skin.

Description

technical field [0001] The invention belongs to the field of chemical pesticides, and in particular relates to a crystal form of N,N-diethyl-2-hydroxy-2-phenylacetamide, a preparation method and application thereof. Background technique [0002] Compound N,N-diethyl-2-hydroxyl-2-phenylacetamide has the chemical structure of formula (I): [0003] [0004] According to the report of patent DE2714671, the compound is prepared by the following method: add acetyl chloride to mandelic acid to esterify the hydroxyl group, add thionyl chloride to generate an acid chloride compound, then add diethylamine to generate an amide ester compound, and finally add a base Hydrolysis of the ester bond affords the compound of formula (I). However, the synthesis route in this document is relatively long, with a total of four-step reactions, and environmentally unfriendly acetyl chloride and thionyl chloride are used, and high-temperature distillation is mostly used for purification. From the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/34C07C231/02C07C231/24A01N37/36A01P17/00A61K8/42A61K8/34A61K8/46A61K8/36A61K8/365A61K8/26A61K8/92A61K8/67A61Q19/00A61Q19/02A61Q19/08A61Q15/00A61Q17/02A61Q17/00A61P17/10
CPCC07C235/34C07C231/02C07C231/24C07D317/72A01N37/36A61K8/42A61K8/345A61K8/463A61K8/36A61K8/365A61K8/26A61K8/922A61K8/676A61K8/678A61K8/671A61K8/67A61Q19/00A61Q19/02A61Q19/08A61Q15/00A61Q17/02A61Q17/005A61P17/10C07B2200/13
Inventor 刘丹妮张飞李彦张蓓尚玉松王轲轲童薇付喜梅
Owner 北京斯瑞朗文生物科技有限公司
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