CN109836424B - Method for preparing caffeine by methylation of environment-friendly theophylline sodium salt - Google Patents
Method for preparing caffeine by methylation of environment-friendly theophylline sodium salt Download PDFInfo
- Publication number
- CN109836424B CN109836424B CN201910184371.2A CN201910184371A CN109836424B CN 109836424 B CN109836424 B CN 109836424B CN 201910184371 A CN201910184371 A CN 201910184371A CN 109836424 B CN109836424 B CN 109836424B
- Authority
- CN
- China
- Prior art keywords
- caffeine
- sodium salt
- methylation
- theophylline
- theophylline sodium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 title claims abstract description 103
- 229960001948 caffeine Drugs 0.000 title claims abstract description 51
- QVGLHVDBDYLFON-UHFFFAOYSA-M sodium;1,3-dimethylpurin-7-ide-2,6-dione Chemical class [Na+].O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 QVGLHVDBDYLFON-UHFFFAOYSA-M 0.000 title claims abstract description 24
- 238000007069 methylation reaction Methods 0.000 title claims abstract description 17
- 230000011987 methylation Effects 0.000 title claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000000746 purification Methods 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N Dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910000856 hastalloy Inorganic materials 0.000 claims description 5
- 239000012498 ultrapure water Substances 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- 229960000278 Theophylline Drugs 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000004412 Bulk moulding compound Substances 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 206010003549 Asthenia Diseases 0.000 description 1
- 210000003710 Cerebral Cortex Anatomy 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N Cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 229940050176 Methyl Chloride Drugs 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 208000007443 Neurasthenia Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 239000003907 antipyretic analgesic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000711 cancerogenic Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004156 green chemistry Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 230000001035 methylating Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- -1 xanthine alkaloid compound Chemical class 0.000 description 1
Abstract
Description
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201910184371.2A CN109836424B (en) | 2019-03-12 | 2019-03-12 | Method for preparing caffeine by methylation of environment-friendly theophylline sodium salt |
Applications Claiming Priority (1)
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CN201910184371.2A CN109836424B (en) | 2019-03-12 | 2019-03-12 | Method for preparing caffeine by methylation of environment-friendly theophylline sodium salt |
Publications (2)
Publication Number | Publication Date |
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CN109836424A CN109836424A (en) | 2019-06-04 |
CN109836424B true CN109836424B (en) | 2022-04-01 |
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Family Applications (1)
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CN201910184371.2A Active CN109836424B (en) | 2019-03-12 | 2019-03-12 | Method for preparing caffeine by methylation of environment-friendly theophylline sodium salt |
Country Status (1)
Country | Link |
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CN (1) | CN109836424B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN112724143B (en) * | 2021-02-07 | 2022-04-15 | 河北工业大学 | Method for preparing theobromine by methylating 3-methylxanthine |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104892611B (en) * | 2015-05-19 | 2017-03-22 | 青岛科技大学 | Synthetic method of caffeine |
CN105294691B (en) * | 2015-11-23 | 2017-03-08 | 青岛科技大学 | A kind of preparation technology of the semi-synthetic caffeine of environment-friendly type |
CN106046004B (en) * | 2016-06-06 | 2018-05-15 | 上海佰特因医药科技有限公司 | A kind of total synthesis method of 1,3,7,9- tetramethyluric acids |
CN106496227A (en) * | 2016-08-31 | 2017-03-15 | 安徽省润生医药股份有限公司 | A kind of preparation method and its usage of istradefylline |
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2019
- 2019-03-12 CN CN201910184371.2A patent/CN109836424B/en active Active
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Inventor after: Xue Wei Inventor after: Yang Hansen Inventor after: Feng Zhijun Inventor after: Xie Lisha Inventor after: Zhang Min Inventor after: Li Fang Inventor after: Zhang Dongsheng Inventor after: Wang Yanji Inventor before: Xue Wei Inventor before: Yang Hansen Inventor before: Feng Zhijun Inventor before: Xie Lisha Inventor before: Li Fang Inventor before: Zhang Dongsheng Inventor before: Wang Yanji |
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