RU2008143264A - Реакционный реагент для трифторметилирования - Google Patents
Реакционный реагент для трифторметилирования Download PDFInfo
- Publication number
- RU2008143264A RU2008143264A RU2008143264/04A RU2008143264A RU2008143264A RU 2008143264 A RU2008143264 A RU 2008143264A RU 2008143264/04 A RU2008143264/04 A RU 2008143264/04A RU 2008143264 A RU2008143264 A RU 2008143264A RU 2008143264 A RU2008143264 A RU 2008143264A
- Authority
- RU
- Russia
- Prior art keywords
- iron
- acid
- reaction reagent
- trifluoromethylation
- reagent according
- Prior art date
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- 239000012070 reactive reagent Substances 0.000 title 1
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 23
- 238000006692 trifluoromethylation reaction Methods 0.000 claims abstract 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract 18
- 150000002506 iron compounds Chemical class 0.000 claims abstract 11
- 239000002253 acid Substances 0.000 claims abstract 9
- 229910052742 iron Inorganic materials 0.000 claims abstract 7
- 150000002978 peroxides Chemical class 0.000 claims abstract 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000003462 sulfoxides Chemical class 0.000 claims abstract 6
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims abstract 4
- MQLVWQSVRZVNIP-UHFFFAOYSA-L ferrous ammonium sulfate hexahydrate Chemical compound [NH4+].[NH4+].O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O MQLVWQSVRZVNIP-UHFFFAOYSA-L 0.000 claims abstract 4
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims abstract 4
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims abstract 4
- -1 iron(II) tetrafluoroborate Chemical compound 0.000 claims abstract 4
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000002131 composite material Substances 0.000 claims abstract 3
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910021575 Iron(II) bromide Inorganic materials 0.000 claims abstract 2
- 229910021577 Iron(II) chloride Inorganic materials 0.000 claims abstract 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims abstract 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims abstract 2
- OWZIYWAUNZMLRT-UHFFFAOYSA-L iron(2+);oxalate Chemical compound [Fe+2].[O-]C(=O)C([O-])=O OWZIYWAUNZMLRT-UHFFFAOYSA-L 0.000 claims abstract 2
- LNOZJRCUHSPCDZ-UHFFFAOYSA-L iron(ii) acetate Chemical compound [Fe+2].CC([O-])=O.CC([O-])=O LNOZJRCUHSPCDZ-UHFFFAOYSA-L 0.000 claims abstract 2
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims abstract 2
- BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 0.000 claims abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 2
- LFKXWKGYHQXRQA-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;iron Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LFKXWKGYHQXRQA-FDGPNNRMSA-N 0.000 claims 1
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical compound CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 229940116269 uric acid Drugs 0.000 claims 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 abstract 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G49/00—Compounds of iron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
1. Реакционный реагент для трифторметилирования, включающий соединение железа, трифторметилиодид, пероксид и сульфоксид. ! 2. Реакционный реагент для трифторметилирования по п.1, дополнительно включающий кислоту. ! 3. Реакционный реагент для трифторметилирования по п.1 или 2, в котором молярное соотношение соединения железа и трифторметилиодида находится в диапазоне от 1:1 до 1:100. ! 4. Реакционный реагент для трифторметилирования по пп.1-3, в котором молярное соотношение соединения железа и пероксида находится в диапазоне от 1:1 до 1:50. ! 5. Реакционный реагент для трифторметилирования по пп.1-3, в котором молярное соотношение соединения железа и сульфоксида находится в диапазоне от 1:50 до 1:30000. ! 6. Реакционный реагент для трифторметилирования по пп.2 и 3, в котором молярное соотношение соединения железа и кислоты находится в диапазоне от 1:0,001 до 1:50. ! 7. Реакционный реагент для трифторметилирования по пп.1-3, в котором соединение железа представляет собой сульфат железа (II), аммонийсульфат железа(II), тетрафторборат железа(II), хлорид железа(II), бромид железа(II), иодид железа(II), ацетат железа(II), оксалат железа(II), бис(ацетилацетонат) железа(II), ферроцен, бис(ŋ5-пентаметилциклопентадиенил)железо или порошок железа. ! 8. Реакционный реагент для трифторметилирования по пп.1-3, в котором соединение железа представляет собой сульфат железа(II), аммонийсульфат железа(II), тетрафторборат железа(II), ферроцен, бис(ŋ5-пентаметилциклопентадиенил)железо или порошок железа. ! 9. Реакционный реагент для трифторметилирования по пп.1-3, в котором пероксид представляет собой пероксид водорода, композит пероксид водорода-мочевина, трет-бутилпероксид или п�
Claims (14)
1. Реакционный реагент для трифторметилирования, включающий соединение железа, трифторметилиодид, пероксид и сульфоксид.
2. Реакционный реагент для трифторметилирования по п.1, дополнительно включающий кислоту.
3. Реакционный реагент для трифторметилирования по п.1 или 2, в котором молярное соотношение соединения железа и трифторметилиодида находится в диапазоне от 1:1 до 1:100.
4. Реакционный реагент для трифторметилирования по пп.1-3, в котором молярное соотношение соединения железа и пероксида находится в диапазоне от 1:1 до 1:50.
5. Реакционный реагент для трифторметилирования по пп.1-3, в котором молярное соотношение соединения железа и сульфоксида находится в диапазоне от 1:50 до 1:30000.
6. Реакционный реагент для трифторметилирования по пп.2 и 3, в котором молярное соотношение соединения железа и кислоты находится в диапазоне от 1:0,001 до 1:50.
7. Реакционный реагент для трифторметилирования по пп.1-3, в котором соединение железа представляет собой сульфат железа (II), аммонийсульфат железа(II), тетрафторборат железа(II), хлорид железа(II), бромид железа(II), иодид железа(II), ацетат железа(II), оксалат железа(II), бис(ацетилацетонат) железа(II), ферроцен, бис(ŋ5-пентаметилциклопентадиенил)железо или порошок железа.
8. Реакционный реагент для трифторметилирования по пп.1-3, в котором соединение железа представляет собой сульфат железа(II), аммонийсульфат железа(II), тетрафторборат железа(II), ферроцен, бис(ŋ5-пентаметилциклопентадиенил)железо или порошок железа.
9. Реакционный реагент для трифторметилирования по пп.1-3, в котором пероксид представляет собой пероксид водорода, композит пероксид водорода-мочевина, трет-бутилпероксид или пероксиуксусную кислоту.
10. Реакционный реагент для трифторметилирования по пп.1-3, в котором пероксид представляет собой пероксид водорода или композит пероксид водорода-мочевина.
11. Реакционный реагент для трифторметилирования по пп.1-3, в котором сульфоксид представляет собой диметилсульфоксид, дибутилсульфоксид или дифенилсульфоксид.
12. Реакционный реагент для трифторметилирования по пп.1-3, в котором сульфоксид представляет собой диметилсульфоксид.
13. Реакционный реагент для трифторметилирования по пп.2 и 3, в котором кислота представляет собой серную кислоту, хлористоводородную кислоту, бромистоводородную кислоту, йодистоводородную кислоту, азотную кислоту, фосфорную кислоту, гексафторфосфорную кислоту, тетрафторборную кислоту, муравьиную кислоту, уксусную кислоту, пропионовую кислоту, щавелевую кислоту, пара-толуолсульфокислоту, трифторметансульфоновую кислоту или трифторуксусную кислоту.
14. Реакционный реагент для трифторметилирования по пп.2 и 3, в котором кислота представляет собой серную кислоту, тетрафторборную кислоту или трифторметансульфоновую кислоту.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006-300571 | 2006-11-06 | ||
| JP2006300571 | 2006-11-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008143264A true RU2008143264A (ru) | 2010-05-10 |
| RU2437868C2 RU2437868C2 (ru) | 2011-12-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008143264/04A RU2437868C2 (ru) | 2006-11-06 | 2007-11-06 | Реакционный реагент для трифторметилирования |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7981318B2 (ru) |
| EP (1) | EP2080744A4 (ru) |
| JP (1) | JP5189345B2 (ru) |
| KR (1) | KR20090083847A (ru) |
| CN (1) | CN101437778A (ru) |
| AU (1) | AU2007318576A1 (ru) |
| BR (1) | BRPI0711100A2 (ru) |
| CA (1) | CA2644333C (ru) |
| MX (1) | MX2008013999A (ru) |
| RU (1) | RU2437868C2 (ru) |
| TW (1) | TWI436964B (ru) |
| WO (1) | WO2008056677A1 (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7884202B2 (en) | 2005-11-09 | 2011-02-08 | Tosoh Corporation | Nucleobase having perfluoroalkyl group and process for producing the same |
| JP5106048B2 (ja) * | 2006-11-06 | 2012-12-26 | 東ソー株式会社 | パーフルオロアルキル基を有するベンゼン類の製造方法 |
| EP2447239A1 (en) | 2010-10-29 | 2012-05-02 | Saltigo GmbH | Copper-catalysed process for the production of substituted or unsubstituted trifluormethylated aryl and heteroaryl compounds |
| JP5924984B2 (ja) * | 2012-03-06 | 2016-05-25 | 国立大学法人東京農工大学 | トリフルオロメチルピリジノン化合物およびその製造方法 |
| CN103553857B (zh) * | 2013-10-29 | 2016-01-20 | 南京大学 | 一种制备邻三氟甲基苯胺或其衍生物的方法 |
| CN112062681A (zh) * | 2020-07-24 | 2020-12-11 | 浙江工业大学 | 三氟甲基化苯胺类化合物的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226449A (en) * | 1962-06-06 | 1965-12-28 | Du Pont | Process for preparing perfluoroalkyl iodides |
| US3271441A (en) | 1962-06-18 | 1966-09-06 | Du Pont | Process for preparing fluoroalkyl substituted aromatic compounds |
| EP0206951B1 (fr) * | 1985-05-22 | 1990-03-21 | Rhone-Poulenc Chimie | Procédé de perfluoroalkylation de dérivés aromatiques |
| US6464895B2 (en) * | 1995-03-24 | 2002-10-15 | Rhodia Chimie | Reagent and process which are useful for grafting a substituted difluoromethyl group onto a compound containing at least one electrophilic function |
| US6215021B1 (en) * | 1998-06-17 | 2001-04-10 | Idaho Research Foundation, Inc. | Trifluoromethylating reagents and synthesizing processes |
| IL147272A0 (en) * | 1999-06-29 | 2002-08-14 | Mitsubishi Chem Corp | Pyrazole derivatives and process for producing the same, and pesticides containing the same as the active ingredient |
| ATE318808T1 (de) * | 2000-07-31 | 2006-03-15 | Nihon Nohyaku Co Ltd | Pyrazolderivat, schädlingsbekämpfungsmittel, das dieses als wirkstoff umfasst und verfahren zu seiner herstellung |
| US7087789B2 (en) * | 2003-01-13 | 2006-08-08 | University Of Southern California | Methods for nucleophilic fluoromethylation |
| US7655641B2 (en) * | 2003-02-14 | 2010-02-02 | Eli Lilly And Company | Sulfonamide derivatives as PPAR modulators |
| PE20050347A1 (es) * | 2003-08-26 | 2005-05-04 | Teijin Pharma Ltd | Derivados de pirrolopirimidina |
| GB0328024D0 (en) * | 2003-12-03 | 2004-01-07 | Glaxo Group Ltd | Compounds |
| JP4587217B2 (ja) | 2005-04-18 | 2010-11-24 | アルパイン株式会社 | 夜間走行支援ナビゲーション装置 |
| JP5053622B2 (ja) * | 2005-11-09 | 2012-10-17 | 東ソー株式会社 | パーフルオロアルキル基を有する核酸塩基類およびその製造方法 |
| US7884202B2 (en) * | 2005-11-09 | 2011-02-08 | Tosoh Corporation | Nucleobase having perfluoroalkyl group and process for producing the same |
-
2007
- 2007-11-06 WO PCT/JP2007/071575 patent/WO2008056677A1/ja not_active Ceased
- 2007-11-06 CA CA2644333A patent/CA2644333C/en not_active Expired - Fee Related
- 2007-11-06 KR KR1020087024516A patent/KR20090083847A/ko not_active Abandoned
- 2007-11-06 EP EP07831307A patent/EP2080744A4/en not_active Withdrawn
- 2007-11-06 AU AU2007318576A patent/AU2007318576A1/en not_active Abandoned
- 2007-11-06 MX MX2008013999A patent/MX2008013999A/es active IP Right Grant
- 2007-11-06 BR BRPI0711100-2A patent/BRPI0711100A2/pt not_active IP Right Cessation
- 2007-11-06 CN CNA2007800158206A patent/CN101437778A/zh active Pending
- 2007-11-06 JP JP2007288135A patent/JP5189345B2/ja not_active Expired - Fee Related
- 2007-11-06 US US12/225,249 patent/US7981318B2/en not_active Expired - Fee Related
- 2007-11-06 RU RU2008143264/04A patent/RU2437868C2/ru not_active IP Right Cessation
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2008
- 2008-04-14 TW TW097113501A patent/TWI436964B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007318576A1 (en) | 2008-05-15 |
| MX2008013999A (es) | 2008-11-12 |
| US20100230633A1 (en) | 2010-09-16 |
| RU2437868C2 (ru) | 2011-12-27 |
| JP2008137993A (ja) | 2008-06-19 |
| EP2080744A1 (en) | 2009-07-22 |
| CA2644333A1 (en) | 2008-05-15 |
| US7981318B2 (en) | 2011-07-19 |
| KR20090083847A (ko) | 2009-08-04 |
| EP2080744A4 (en) | 2010-03-24 |
| TW200942508A (en) | 2009-10-16 |
| WO2008056677A1 (en) | 2008-05-15 |
| BRPI0711100A2 (pt) | 2011-08-23 |
| TWI436964B (zh) | 2014-05-11 |
| CA2644333C (en) | 2014-05-06 |
| CN101437778A (zh) | 2009-05-20 |
| JP5189345B2 (ja) | 2013-04-24 |
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