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Synthesis process of gliclazide intermediate 2-formamide cyclohexanone

A synthesis process, the technology of cyclohexanone, which is applied in the field of synthesis of gliclazide intermediates, can solve the problems of environmental pollution, waste of catalysts, high energy consumption under high temperature reaction conditions of xylene, etc., and achieve the effect of high purity and low energy consumption

Pending Publication Date: 2021-04-16
ANHUI JINDING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route uses cyclohexanone as a raw material and is obtained by condensation with urea under catalytic conditions. Ketones were synthesized into 2-carboxamide cyclohexanone by two-step reaction. The study found that the best mass ratio of cyclohexanone, urea, ammonium carbonate and xylene was 50:18:9:25 under the condition of no catalyst. The condensation reaction generates a spiro ring, and the spiro ring is hydrolyzed in dilute sulfuric acid with a pH value of 1.4-2.0 to obtain a white crystalline solid 2-carboxamide cyclohexanone with a yield of 54.6%.
[0003] The synthesis process of 2-carboxamide cyclohexanone in the prior art does not catalyze cyclohexanone and urea to generate spiro ring intermediates with high selectivity of catalyst, and the high temperature reaction condition of xylene consumes a lot of energy, so further research is still needed to improve Yield and purity of 2-carboxamide cyclohexanone

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The synthesis process of the gliclazide intermediate 2-carboxamide cyclohexanone in this embodiment comprises the following steps:

[0020] a. Cool the reaction kettle to -15°C in advance with ice ethanol, add 902kg of xylene and 60kg of urea, add catalyst tetrabutyl titanate 17.02kg under mechanical stirring, keep the reaction temperature at -15°C, slowly add cyclohexanone 225.72 kg, the dropping time was kept for 2 hours, and after the dropping was completed, the temperature was kept at -8°C for 21 hours;

[0021] b. Warm up the reaction kettle to 3°C, add a small amount of water and stir for 26 minutes, let stand to separate layers, extract with water 3 times, remove water with anhydrous magnesium sulfate, and filter under reduced pressure to obtain the filtrate; the pressure of the reduced-pressure filter is -0.085MPa .

[0022] c. Concentrate the filtrate under reduced pressure to recover xylene to obtain the concentrated filtrate, add ethanol and sodium bicarbona...

Embodiment 2

[0024] The synthesis process of the gliclazide intermediate 2-carboxamide cyclohexanone in this embodiment comprises the following steps:

[0025] a. Cool the reaction kettle to -13°C in advance with ice ethanol, add 1080kg of xylene and 60kg of urea, add catalyst tetrabutyl titanate 16.34kg under mechanical stirring, keep the reaction temperature at -13°C, slowly add cyclohexanone 215.91 kg, the dropping time was kept for 2.2 hours, and after the dropping was completed, the temperature was kept at -7°C for 20 hours;

[0026] b. Warm up the reaction kettle to 0°C, add a small amount of water and stir for 25 minutes, let stand to separate layers, extract with water 4 times, remove water with anhydrous magnesium sulfate, and filter under reduced pressure to obtain the filtrate; the pressure of the reduced-pressure filter is -0.092MPa .

[0027] c. Concentrate the filtrate under reduced pressure to recover xylene to obtain the concentrated filtrate, add ethanol and aqueous sodiu...

Embodiment 3

[0029] The synthesis process of the gliclazide intermediate 2-carboxamide cyclohexanone in this embodiment comprises the following steps:

[0030] a. Cool the reaction kettle to -16°C with ice alcohol in advance, add 1300kg of xylene and 60kg of urea, add catalyst tetrabutyl titanate 18.72kg under mechanical stirring, keep the reaction temperature at -16°C, slowly add cyclohexanone 235.54 kg, the dropping time was kept for 1.8 hours, and after the dropping was completed, the temperature was kept at -6°C for 22 hours;

[0031] b. The temperature of the reaction kettle was raised to -3°C, and a small amount of water was added to stir for 22 minutes. After standing for stratification, water was extracted 3 times, and the water was removed by anhydrous magnesium sulfate, and the filtrate was obtained by vacuum filtration; the pressure of vacuum filtration was -0.095 MPa;

[0032] c. Concentrate the filtrate under reduced pressure to recover xylene to obtain the concentrated filtr...

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Abstract

The invention provides a synthesis process of a gliclazide intermediate 2-formamide cyclohexanone, and relates to the technical field of synthesis of gliclazide intermediates. According to the synthesis process disclosed by the invention, after the reaction kettle is cooled in advance, the solvent xylene and the raw material urea are added and the catalyst tetrabutyl titanate is added, the spiro intermediate can be generated through high-selectivity catalysis along with the addition of cyclohexanone, and the reaction condition of high-temperature azeotropy is not needed; ketone can be hydrolyzed and removed only at a low temperature after heating, water adding and stirring are carried out; after xylene and residual cyclohexanone are removed from the filtrate through vacuum concentration, ethanol is used for dispersing the crude product of the 2formamide cyclohexanone, and sodium bicarbonate is used for neutralizing generated hydrogen ions, so that the neutral environment of the system is maintained, and a pure product of the 2-formamide cyclohexanone with high yield and purity is obtained after subsequent filtration and crystallization.

Description

technical field [0001] The invention relates to the technical field of synthesis of gliclazide intermediates, in particular to a synthesis process of gliclazide intermediate 2-carboxamide cyclohexanone. Background technique [0002] 2-Carboxamide cyclohexanone is the raw material for the manufacture of herbicides and the synthesis of the drug gliclazide for the treatment of type II diabetes. At present, only the cyclohexanone route is suitable for industrial production. This route uses cyclohexanone as a raw material and is obtained by condensation with urea under catalytic conditions. Ketones were synthesized into 2-carboxamide cyclohexanone by two-step reaction. The study found that the best mass ratio of cyclohexanone, urea, ammonium carbonate and xylene was 50:18:9:25 under the condition of no catalyst. The condensation reaction generates a spiro ring, and the spiro ring is hydrolyzed in dilute sulfuric acid with a pH value of 1.4-2.0 to obtain a white crystalline solid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/82C07C231/10
Inventor 蒋爱萍
Owner ANHUI JINDING PHARMA
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