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One-pot synthesis method of N-hydrocarbon acyl cyclic lactam derivative

A technology for a hydrocarbon acyl cyclic lactam and a synthesis method, which is applied in the field of one-pot synthesis of N-hydrocarbon acyl cyclic lactam derivatives, can solve the problems of harsh reaction conditions, high reaction temperature, short production cycle and the like, and achieves easy reaction, Simple operation, short process effect

Active Publication Date: 2014-05-28
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention mainly aims at the problems of high reaction temperature, complex process, harsh reaction conditions and low yield in the preparation method of N-hydrocarbyl cyclic lactam derivatives in the prior art, and aims to provide a kind of N-hydrocarbyl cyclic lactam derivative preparation method with mild reaction conditions and high yield. , Low-cost one-pot synthesis of N-hydrocarbyl cyclic lactam derivatives, the method is easy to operate, the production cycle is short, and it meets industrial production

Method used

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  • One-pot synthesis method of N-hydrocarbon acyl cyclic lactam derivative
  • One-pot synthesis method of N-hydrocarbon acyl cyclic lactam derivative
  • One-pot synthesis method of N-hydrocarbon acyl cyclic lactam derivative

Examples

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Effect test

Embodiment 1

[0054] Preparation of 6-octylamidohexyl hydroxamic acid

[0055] Control the temperature of the reactor at 30°C, add 11.32 parts of caprolactam with a purity of 99% and 19.44 parts of octanoyl chloride with a purity of 99% into the reactor, add 22.64 parts of dichloromethane as a solvent, and divide 10.08 parts of sodium bicarbonate under stirring Multiple batches were added to the reactor, and after 3 hours of reaction; then 6.95 parts of hydroxylamine hydrochloride and 21.20 parts of sodium carbonate were added to the above-mentioned reactor, and 23.7 parts of methanol were added as a solvent for a further 3 hours of reaction to obtain the required 6-n- The product of decanoylaminohexyl hydroxamate is adjusted to a pH value of about 5 with hydrochloric acid solution to obtain 6-n-decylamidohexylhydroxamic acid. Analysis showed that the purity of 6-n-octylamidohexyl hydroxamic acid was 87.3%, and the yield was 90.4%. Product Mr: 272.21, detected by LC-MS MS: 273.1 ( Figure...

Embodiment 2

[0057] Preparation of 6-benzamidohexyl hydroxamic acid

[0058] Control the temperature of the reactor at 25°C, add 11.32 parts of caprolactam with a purity of 99% and 16.80 parts of benzoyl chloride with a purity of 99% into the reactor, add 45 parts of dichloromethane as a solvent, and divide 6.8 parts of calcium oxide under stirring Add multiple batches to the reactor, and react for 1 hour; then add 6.95 parts of hydroxylamine hydrochloride and 21.20 parts of sodium carbonate to the above reactor, and add 23.7 parts of methanol as a solvent, and react for a further 2 hours to obtain 6-benzamide Base hexyl hydroxamate product, adjust the pH value to about 5 with nitric acid solution to obtain 6-benzamidohexyl hydroxamic acid. Analysis showed that the purity of 6-benzamidohexyl hydroxamic acid was 86.4%, and the yield was 90.2%. Product Mr: 250.13, detected by LC-MS MS: 249.9 ( Image 6 ).

Embodiment 3

[0060] Preparation of 6-n-Dodecylamidohexyl Hydroxamic Acid

[0061] The temperature of the reactor in Example 1 was adjusted to 15° C., 19.44 parts of octanoyl chloride was changed to 26.17 parts of dodecanoyl chloride, and other conditions remained unchanged, and the obtained 6-n-dodecanoylhexyl hydroxamic acid product was obtained. Analysis showed a purity of 85.4% and a yield of 88.2%. Product Mr: 328.21, detected by mass spectrometry MS: 329.2 ( Figure 7 ), the product is 1 H NMR ( image 3 )with 13 C NMR ( Figure 4 ) was confirmed as the structure of the desired product.

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Abstract

The invention discloses a one-pot synthesis method of an N-hydrocarbon acyl cyclic lactam derivative. The method comprises the following steps: adding lactam and acyl chloride into a reaction kettle, stirring, performing N-acylation reaction, slowly adding a weak alkali compound into the reaction kettle to neutralize acid generated in the N-acylation reaction, reacting for a while, further adding hydroxylamine and a weak alkali compound or only adding the weak alkali compound into the reaction kettle, and performing open loop reaction to obtain a N-hydrocarbon acylamino hydroximic acid salt or N-hydrocarbon acylamino carboxylate. The method adopts a one-pot synthesis method, is gentle in reaction condition, high in yield, low in cost, easy to operate and short in production period, and the industrial production is met.

Description

technical field [0001] The invention relates to a one-pot synthesis method of N-hydrocarbyl cyclic lactam derivatives, and belongs to the field of synthesis of metal ore flotation collectors. Background technique [0002] Hydroxamic and carboxylic acids are known flotation collectors for the froth flotation of oxide minerals and are commonly used in the flotation of metallic minerals. N-hydrocarbon amido hydroxamic acid derivatives and N-hydrocarbon amido carboxylic acid derivatives contain two functional groups, namely amide group and hydroxamic acid group or carboxylic acid group, both of which can interact with metal ions Forms chelates, thus increasing its flotation collection performance in oxidized ores. [0003] Compounds such as hydroxamic acid or carboxylic acid containing substituted amide groups in the molecule are the most extensively studied class of HDAC inhibitors so far. HDAC is currently receiving extensive attention as a potential anticancer and anti-infla...

Claims

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Application Information

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IPC IPC(8): C07C259/06C07C233/47C07C231/10B03D1/01B03D101/02
Inventor 钟宏邓兰青王帅刘广义曹占芳
Owner CENT SOUTH UNIV
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