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Preparation method of methyl orotate

A technology of methyl orotic acid and orotic acid, which is applied in the field of preparation of methyl orotic acid, can solve the problems of high consumption of raw materials, high labor intensity, difficulty in scaling up production, etc. High strength, reduced dosage effect

Inactive Publication Date: 2016-02-03
CHANGZHOU VOCATIONAL INST OF ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wherein the Fischer esterification method directly carries out the reversible reaction of orotic acid and methanol under the situation that hydrogen chloride is a catalyst, the reaction time is long, the reaction temperature is high, and the yield is low; The thionyl chloride needs to be evaporated before the esterification reaction, the labor intensity is high, the raw material consumption is large, and more pollution will be generated, so it is difficult to scale up the production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Put orotic acid (78.0 g, 0.50 mol), toluene (200 g), and 5 drops of N,N-dimethylformamide into a 500 mL four-necked flask, and stir to raise the temperature to 80°C. Start to add thionyl chloride (77.5g, 0.65mol) dropwise at 80°C. Hydrochloric acid gas will come out during the dropwise addition (note the drying and recovery of hydrochloric acid gas). When the temperature rises to 83°C, the bubbles will become larger, and continue to drop about 1.5 The hour dropwise addition was completed. After the dropwise addition was completed, the temperature was raised to reflux at 110°C for 8 hours. TLC confirmed that no raw material remained, and an acid chloride intermediate was obtained.

[0013] After the reaction was completed, the temperature was lowered to 60°C under the protection of nitrogen, and excess methanol (90.0g, 2.8mol) was added dropwise to the original reaction system, exothermic. . After the reaction was completed, the product was cooled and suction filtered,...

Embodiment 2

[0015] Put orotic acid (78.0 g, 0.50 mol), toluene (200 g), and 5 drops of N,N-dimethylformamide into a 500 mL four-necked flask, and stir to raise the temperature to 80°C. Start to add thionyl chloride (71.5g, 0.60mol) dropwise at 80°C. Hydrochloric acid gas comes out during the dropwise addition (note that the gas is dried and recovered), and the bubbles become larger when the temperature rises to 83°C. Continue to add about 1.5 pieces The hour dropwise addition was completed. After the dropwise addition was completed, the reaction was carried out at 80°C under reflux for 8 hours. TLC confirmed that no raw material remained, and the acid chloride intermediate was obtained.

[0016] After the reaction was completed, the temperature was lowered to 60°C under the protection of nitrogen, and excess methanol (90.0g, 2.8mol) was added dropwise to the original reaction system, exothermic. . After the reaction was completed, the product was cooled and suction filtered, washed with...

Embodiment 3

[0018] Put orotic acid (78.0 g, 0.50 mol), toluene (200 g), and 5 drops of N,N-dimethylformamide into a 500 mL four-necked flask, and stir to raise the temperature to 80°C. Start to add thionyl chloride (83.5g, 0.70mol) dropwise at 80°C. During the dropwise addition, hydrochloric acid gas will emerge (note the drying and recovery of hydrochloric acid gas). When the temperature rises to 83°C, the bubbles will become larger, and continue to drop about 1.5 The hour dropwise addition was completed. After the dropwise addition was completed, the temperature was raised to reflux at 110°C for 8 hours. TLC confirmed that no raw material remained, and an acid chloride intermediate was obtained.

[0019] After the reaction was completed, the temperature was lowered to 60°C under the protection of nitrogen, and excess methanol (90.0g, 2.8mol) was added dropwise to the original reaction system, exothermic. . After the reaction was completed, the product was cooled and suction filtered, ...

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PUM

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Abstract

The invention relates to a preparation method of methyl orotate. The preparation method comprises the following steps: adding orotic acid, toluene and N,N-dimethylformamide to a reaction vessel, dropwise adding slightly excessive thionyl chloride and carrying out reflux reaction, thus preparing an acyl chlorination intermediate; dropwise adding ethanol to the reaction system, carrying out reflux reaction and carrying out cooling and suction filtration, thus preparing methyl orotate. The preparation method has the beneficial effects that the green and clean process production technology is adopted; orotic acid is used as the raw material, toluene is used as a solvent and slightly excessive thionyl chloride is added to carry out acyl chlorination to prepare the acyl chloride intermediate, thus reducing the usage amount of thionyl chloride, solving the problems of high operating labor intensity and severe pollution caused because excessive thionyl chloride needs to be removed through distillation and providing technical support for the economical, environment-friendly and clean process production technology and volume production of methyl orotate.

Description

technical field [0001] The invention relates to a preparation method of methyl orotate. Background technique [0002] Methyl orotate is a key intermediate in the preparation of polypeptide series, and its preparation methods have been reported in many literatures, mainly including Fischer esterification and acyl chloride. Wherein the Fischer esterification method directly carries out the reversible reaction of orotic acid and methanol under the situation that hydrogen chloride is a catalyst, the reaction time is long, the reaction temperature is high, and the yield is low; The thionyl chloride needs to be evaporated before the esterification reaction, which is labor-intensive, consumes a lot of raw materials, will produce more pollution, and is difficult to scale up production. Contents of the invention [0003] The technical problem to be solved in the present invention is: based on the above-mentioned problem, the present invention provides a kind of preparation method ...

Claims

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Application Information

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IPC IPC(8): C07D239/557
CPCC07D239/557
Inventor 程进刘长春薛叙明
Owner CHANGZHOU VOCATIONAL INST OF ENG
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