CN103880699A - Method for synthesizing imides compounds - Google Patents
Method for synthesizing imides compounds Download PDFInfo
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- CN103880699A CN103880699A CN201410142432.6A CN201410142432A CN103880699A CN 103880699 A CN103880699 A CN 103880699A CN 201410142432 A CN201410142432 A CN 201410142432A CN 103880699 A CN103880699 A CN 103880699A
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- 238000000034 method Methods 0.000 title claims abstract description 11
- -1 imides compounds Chemical class 0.000 title abstract description 17
- 230000002194 synthesizing effect Effects 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 238000010189 synthetic method Methods 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 239000012752 auxiliary agent Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000010898 silica gel chromatography Methods 0.000 claims description 9
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 8
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000002474 experimental method Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 229910021577 Iron(II) chloride Inorganic materials 0.000 abstract 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 150000003949 imides Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229940059260 amidate Drugs 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical class Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UXKCLTPQRBKROC-UHFFFAOYSA-N C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C1=CC=CC=C1.[P] Chemical group C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C1=CC=CC=C1.[P] UXKCLTPQRBKROC-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000010499 C–H functionalization reaction Methods 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000032825 Ring chromosome 2 syndrome Diseases 0.000 description 1
- ZYPGADGCNXOUJP-CXVPHVKISA-N Variotin Chemical compound CCCC[C@@H](O)\C=C(/C)\C=C\C=C\C(=O)N1CCCC1=O ZYPGADGCNXOUJP-CXVPHVKISA-N 0.000 description 1
- XSWALQKVYPLUJA-UHFFFAOYSA-N [Ru].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Ru].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 XSWALQKVYPLUJA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- ZYPGADGCNXOUJP-UHFFFAOYSA-N dl-Variotin Natural products CCCCC(O)C=C(C)C=CC=CC(=O)N1CCCC1=O ZYPGADGCNXOUJP-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (9)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510101920.7A CN104725266B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201410142432.6A CN103880699B (en) | 2014-04-10 | 2014-04-10 | Method for synthesizing imides compounds |
CN201510101941.9A CN104788336B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101942.3A CN104788337B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101939.1A CN104788335B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101921.1A CN104744290B (en) | 2014-04-10 | 2014-04-10 | A kind of synthetic method of imide analog compounds |
CN201510101936.8A CN104725267B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN201410142432.6A CN103880699B (en) | 2014-04-10 | 2014-04-10 | Method for synthesizing imides compounds |
Related Child Applications (6)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510101920.7A Division CN104725266B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101942.3A Division CN104788337B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101941.9A Division CN104788336B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101936.8A Division CN104725267B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101921.1A Division CN104744290B (en) | 2014-04-10 | 2014-04-10 | A kind of synthetic method of imide analog compounds |
CN201510101939.1A Division CN104788335B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
Publications (2)
Publication Number | Publication Date |
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CN103880699A true CN103880699A (en) | 2014-06-25 |
CN103880699B CN103880699B (en) | 2015-04-08 |
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CN201410142432.6A Active CN103880699B (en) | 2014-04-10 | 2014-04-10 | Method for synthesizing imides compounds |
CN201510101942.3A Active CN104788337B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101939.1A Active CN104788335B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101941.9A Active CN104788336B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101921.1A Active CN104744290B (en) | 2014-04-10 | 2014-04-10 | A kind of synthetic method of imide analog compounds |
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CN201510101942.3A Active CN104788337B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101939.1A Active CN104788335B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101941.9A Active CN104788336B (en) | 2014-04-10 | 2014-04-10 | The synthetic method of imide analog compounds |
CN201510101921.1A Active CN104744290B (en) | 2014-04-10 | 2014-04-10 | A kind of synthetic method of imide analog compounds |
Country Status (1)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023056957A1 (en) * | 2021-10-09 | 2023-04-13 | 中国石油化工股份有限公司 | Working solution for producing hydrogen peroxide by means of anthraquinone method and solvent system thereof |
CN115960008A (en) * | 2021-10-09 | 2023-04-14 | 中国石油化工股份有限公司 | Synthesis method of imide derivative |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115806502B (en) * | 2022-12-29 | 2024-02-23 | 杭州百凯生物医药有限公司 | Alpha-amidoketone derivative and preparation method and application thereof |
Family Cites Families (3)
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FR2966248B1 (en) * | 2010-10-18 | 2020-05-01 | Centre National De La Recherche Scientifique (Cnrs) | METHOD FOR FUNCTIONALIZING SURFACES FOR THE DETECTION OF ANALYTES |
CN101985415B (en) * | 2010-11-11 | 2013-01-02 | 江南大学 | Preparation method of verbenol and verbenone through air oxidation of a-pinene at room temperature |
CN102516138A (en) * | 2011-10-31 | 2012-06-27 | 成都理工大学 | N-aryl t-butyl sulfonamide, synthetic method and application thereof |
-
2014
- 2014-04-10 CN CN201410142432.6A patent/CN103880699B/en active Active
- 2014-04-10 CN CN201510101942.3A patent/CN104788337B/en active Active
- 2014-04-10 CN CN201510101939.1A patent/CN104788335B/en active Active
- 2014-04-10 CN CN201510101941.9A patent/CN104788336B/en active Active
- 2014-04-10 CN CN201510101921.1A patent/CN104744290B/en active Active
Non-Patent Citations (3)
Title |
---|
FENG WANG, ET AL.: "Highly Efficient Iron(II) Chloride/N-Bromosuccinimide-Mediated Synthesis of Imides and Acylsulfonamides", 《ADV. SYNTH. CATAL.》 * |
JING WANG, ET AL.: "Fe-Catalysed oxidative C–H/N–H coupling between aldehydes and simple amides", 《CHEM. COMMUN.》 * |
YONG-JUN BIAN, ET AL.: "Synthesis of Imides by Palladium-Catalyzed C H Functionalization of Aldehydes with Secondary Amides", 《CHEM. EUR. J.》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023056957A1 (en) * | 2021-10-09 | 2023-04-13 | 中国石油化工股份有限公司 | Working solution for producing hydrogen peroxide by means of anthraquinone method and solvent system thereof |
CN115960008A (en) * | 2021-10-09 | 2023-04-14 | 中国石油化工股份有限公司 | Synthesis method of imide derivative |
Also Published As
Publication number | Publication date |
---|---|
CN104744290B (en) | 2016-07-13 |
CN104788337A (en) | 2015-07-22 |
CN104788335A (en) | 2015-07-22 |
CN104788335B (en) | 2016-09-28 |
CN104788337B (en) | 2016-09-28 |
CN103880699B (en) | 2015-04-08 |
CN104788336A (en) | 2015-07-22 |
CN104788336B (en) | 2016-11-30 |
CN104744290A (en) | 2015-07-01 |
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Application publication date: 20140625 Assignee: Hunan Sipaike Material Technology Co., Ltd. Assignor: Shen Jun Contract record no.: 2015440020194 Denomination of invention: Method for synthesizing imides compounds Granted publication date: 20150408 License type: Exclusive License Record date: 20150528 |
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