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Synthesis and preparation method of phenobarbital-d5 for qualitative and quantitative use in forensic science

A phenobarbital and scientific technology, applied in the field of preparation of a D5-deuterated phenobarbital standard in the field of forensic science, can solve the problem of poor stability of the deuterated internal standard, dependence on imports, restrictions on widespread use, etc. problems, to achieve the effect of eliminating hidden safety hazards, good quality and low cost

Active Publication Date: 2021-06-22
INST OF FORENSIC SCI OF MIN OF PUBLIC SECURITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The stability of the deuterated internal standard substance is poor. Our country has not yet broken through this technical bottleneck restricting the production of deuterated substances in our country. There is no manufacturer producing the deuterated substances involved in the poisonous substance involved. The use of this product can only rely on imports
For a long time, the deuterated internal standards used in my country have been dependent on imports, which seriously limits the wide use of such standard products in China

Method used

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  • Synthesis and preparation method of phenobarbital-d5 for qualitative and quantitative use in forensic science
  • Synthesis and preparation method of phenobarbital-d5 for qualitative and quantitative use in forensic science
  • Synthesis and preparation method of phenobarbital-d5 for qualitative and quantitative use in forensic science

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Experimental program
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Effect test

Embodiment 1

[0032] (1) Dimethyl 2-phenylmalonate (10.00mmol, 2.08g) was placed in a 50mL round bottom flask, the solvent MeOH (30mL) was added, and MeONa (15.00mmol, 0.81g) was added, and stirred at room temperature for 1h . Then deuterated bromoethane (14.00 mmol, 1.60 g) was added, stirred at room temperature for 5 h, and the reaction was monitored by TLC until dimethyl 2-phenylmalonate disappeared.

[0033] (2) Continue to add MeONa (25.00mmol, 1.35g) and urea (16mmol, 0.96g) to the reaction system, heat the reaction mixture to reflux rapidly, stir for 1h, recover methanol by distillation under reduced pressure, and add 30mL of urea to the residue Stir the water evenly, add hydrochloric acid (concentration: 6mol / L) to adjust the pH to 2. Then extract three times with ethyl acetate, extract with 30mL ethyl acetate each time, combine the organic phases and dry with anhydrous sodium sulfate (40g), after filtering, concentrate under reduced pressure, column chromatography purification, el...

Embodiment 2

[0035](1) Diethyl 2-phenylmalonate (100.00mmol, 23.6g) was placed in a 500mL round bottom flask, the solvent EtOH (300mL) was added, the temperature was cooled to 0°C in an ice bath, and then EtONa (140.0mmol, 9.5g), stirred for 1h. The reaction system was returned to room temperature, deuterated bromoethane (140.0 mmol, 16.0 g) was added, stirred at room temperature for 5 h, and the reaction was monitored by TLC until the disappearance of diethyl 2-phenylmalonate.

[0036] (2) Continue to add EtONa (250.0mmol, 17.0g) and urea (140mmol, 8.4g) to the reaction system, heat the reaction mixture to reflux rapidly, stir for 1h, reclaim ethanol by distillation under reduced pressure, and add 300mL of urea to the residue Stir the water evenly, add hydrochloric acid (concentration: 6mol / L) to adjust the pH to 2. Then it was extracted three times with ethyl acetate, each extraction was extracted with 300mL ethyl acetate, the combined organic phases were dried with anhydrous sodium sul...

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Abstract

The present invention discloses a synthesis and preparation method of phenobarbital-D5 for qualitative and quantitative use in forensic science, comprising the following steps: (1) using 2-phenylmalonate as raw material, under the action of alkali, 2-phenylmalonate Ester is replaced with deuterobromoethane to obtain 2-(ethyl-D5)-2-phenylmalonate; (2) 2-(ethyl-D5)-2-phenylmalonate The ester is not separated, and the amine transesterification reaction with urea is carried out in situ to obtain D5-deuterated phenobarbital. The synthesis and preparation method of phenobarbital-D5 for qualitative and quantitative use in forensic science of the present application has mild reaction conditions, simple operation, and the yield can reach 70%-80%. The D5-deuterated phenobarbital synthesized by this process The standard product has the advantages of good quality, purity up to 99.768%, and high stability.

Description

technical field [0001] The invention relates to the fields of organic synthesis and chemical analysis and detection, in particular to a preparation method of a D5-deuterated phenobarbital standard in the field of forensic science. Background technique [0002] Phenobarbital alias Gardina, luminal (formula compound III), chemical name 5-ethyl-5-phenyl-2,4,6 (1H, 3H, 5H)-pyrimidinetrione, is a Long-acting barbiturates with sedative, hypnotic, and anticonvulsant effects. It can also resist epilepsy, and has a good effect on grand mal seizures, partial seizures and status epilepticus. However, long-term use of such drugs can produce tolerance and dependence, and poisoning can occur when used repeatedly or in large quantities. In recent years, criminal cases such as poisoning, suicide, and misuse caused by the abuse of such drugs have occurred from time to time. This requires the public security judicial appraisal department to test the samples of samples involving such drugs....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/62C07B59/00
CPCC07B59/002C07B2200/05C07D239/62
Inventor 杜鸿雁宋歌董颖魏春明于忠山任昕昕
Owner INST OF FORENSIC SCI OF MIN OF PUBLIC SECURITY
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