CN101362678B - 一种甲基化反应的方法 - Google Patents
一种甲基化反应的方法 Download PDFInfo
- Publication number
- CN101362678B CN101362678B CN2008101072073A CN200810107207A CN101362678B CN 101362678 B CN101362678 B CN 101362678B CN 2008101072073 A CN2008101072073 A CN 2008101072073A CN 200810107207 A CN200810107207 A CN 200810107207A CN 101362678 B CN101362678 B CN 101362678B
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- CN
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- Prior art keywords
- reaction
- methylation
- nitrogen
- acetonitrile
- methyl
- 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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- 238000007069 methylation reaction Methods 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 10
- 238000010992 reflux Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract 2
- 238000003756 stirring Methods 0.000 claims description 20
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical class COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 claims description 11
- 235000015320 potassium carbonate Nutrition 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- 230000001035 methylating effect Effects 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 238000010907 mechanical stirring Methods 0.000 abstract description 4
- 230000011987 methylation Effects 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- WPXWLDCJSZSAAU-UHFFFAOYSA-N methyl 2,5-dimethylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC(C)=CC=C1C WPXWLDCJSZSAAU-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical class [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 231100000563 toxic property Toxicity 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000000967 suction filtration Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000012065 filter cake Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 240000004922 Vigna radiata Species 0.000 description 3
- 235000010721 Vigna radiata var radiata Nutrition 0.000 description 3
- 235000011469 Vigna radiata var sublobata Nutrition 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GRRIYLZJLGTQJX-UHFFFAOYSA-N 1,2-dibenzoylhydrazine Chemical compound C=1C=CC=CC=1C(=O)NNC(=O)C1=CC=CC=C1 GRRIYLZJLGTQJX-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 239000011259 mixed solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (1)
Priority Applications (1)
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CN2008101072073A CN101362678B (zh) | 2008-09-18 | 2008-09-18 | 一种甲基化反应的方法 |
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CN2008101072073A CN101362678B (zh) | 2008-09-18 | 2008-09-18 | 一种甲基化反应的方法 |
Publications (2)
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CN101362678A CN101362678A (zh) | 2009-02-11 |
CN101362678B true CN101362678B (zh) | 2011-02-16 |
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CN2008101072073A Expired - Fee Related CN101362678B (zh) | 2008-09-18 | 2008-09-18 | 一种甲基化反应的方法 |
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Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102675092B (zh) * | 2011-03-14 | 2014-11-05 | 江苏中丹药物研究有限公司 | 一种制备2-芳基-2,2-二甲基乙酸甲酯的方法 |
CN111234050A (zh) * | 2020-03-20 | 2020-06-05 | 淄博千汇生物科技有限公司 | 甲基倍他环糊精绿色制备工艺 |
CN111440147B (zh) * | 2020-05-19 | 2023-03-07 | 苏州卫生职业技术学院 | N-(2-甲基-5-氨基苯基)-4-(3-吡啶基)-2-嘧啶胺的合成方法 |
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2008
- 2008-09-18 CN CN2008101072073A patent/CN101362678B/zh not_active Expired - Fee Related
Non-Patent Citations (2)
Title |
---|
D.D.REYNOLDS and W.O.KENYON.Preparation and Reactions of Sulfonic Esters. V. Synthesis of Cyclic TertiaryPreparation and Reactions of Sulfonic Esters. V. Synthesis of Cyclic Tertiary Amines..《Journal of the American Chemical Society 》.1950,第72卷1597-1598. * |
张春雷等.含卤素端基的单取代对-叔丁基杯[6]芳烃的合成与表征.《有机化学》.2006,第26卷(第3期),310-313. * |
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CN101362678A (zh) | 2009-02-11 |
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