GB1107881A - Fluorinated pyridines - Google Patents
Fluorinated pyridinesInfo
- Publication number
- GB1107881A GB1107881A GB1038164A GB1038164A GB1107881A GB 1107881 A GB1107881 A GB 1107881A GB 1038164 A GB1038164 A GB 1038164A GB 1038164 A GB1038164 A GB 1038164A GB 1107881 A GB1107881 A GB 1107881A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- reaction
- tetrafluoropyridine
- converted
- compounds
- 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.)
- Expired
Links
- 150000003222 pyridines Chemical class 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 8
- DNDPLEAVNVOOQZ-UHFFFAOYSA-N 2,3,4,5,6-pentachloropyridine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=C1Cl DNDPLEAVNVOOQZ-UHFFFAOYSA-N 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- -1 alkali metal alkoxide Chemical class 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- XTGOWLIKIQLYRG-UHFFFAOYSA-N 2,3,4,5,6-pentafluoropyridine Chemical compound FC1=NC(F)=C(F)C(F)=C1F XTGOWLIKIQLYRG-UHFFFAOYSA-N 0.000 abstract 2
- KQLOCMVTIMEOTK-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-phenylpyridine Chemical compound FC1=NC(F)=C(F)C(C=2C=CC=CC=2)=C1F KQLOCMVTIMEOTK-UHFFFAOYSA-N 0.000 abstract 2
- PKSORSNCSXBXOT-UHFFFAOYSA-N 3,5-dichloro-2,4,6-trifluoropyridine Chemical compound FC1=NC(F)=C(Cl)C(F)=C1Cl PKSORSNCSXBXOT-UHFFFAOYSA-N 0.000 abstract 2
- UZJXVKPEYNNWKU-UHFFFAOYSA-N 3-chloro-2,4,6-trifluoropyridine Chemical compound FC1=CC(F)=C(Cl)C(F)=N1 UZJXVKPEYNNWKU-UHFFFAOYSA-N 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 abstract 2
- ANSZZPJMTBLPCY-UHFFFAOYSA-N (2,3,5,6-tetrafluoropyridin-4-yl)hydrazine Chemical compound NNC1=C(F)C(F)=NC(F)=C1F ANSZZPJMTBLPCY-UHFFFAOYSA-N 0.000 abstract 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- DLOOKZXVYJHDIY-UHFFFAOYSA-N 2,3,4,5-tetrachloropyridine Chemical class ClC1=CN=C(Cl)C(Cl)=C1Cl DLOOKZXVYJHDIY-UHFFFAOYSA-N 0.000 abstract 1
- MVRNAPZMQQYTIN-UHFFFAOYSA-N 2,3,4,5-tetrafluoropyridine Chemical compound FC1=CN=C(F)C(F)=C1F MVRNAPZMQQYTIN-UHFFFAOYSA-N 0.000 abstract 1
- DQUZAWIYRDKTSR-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-(2,3,4,5,6-pentafluorophenyl)pyridine Chemical compound FC1=NC(F)=C(F)C(C=2C(=C(F)C(F)=C(F)C=2F)F)=C1F DQUZAWIYRDKTSR-UHFFFAOYSA-N 0.000 abstract 1
- QOWFVYVULNALJH-UHFFFAOYSA-N 2,3,5-trichloro-4-fluoropyridine Chemical class ClC=1C(=C(C(=NC=1)Cl)Cl)F QOWFVYVULNALJH-UHFFFAOYSA-N 0.000 abstract 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 abstract 1
- AYTUSKIZXVPKBR-UHFFFAOYSA-N 3,5-dichloro-2,6-difluoropyridine Chemical compound FC1=NC(F)=C(Cl)C=C1Cl AYTUSKIZXVPKBR-UHFFFAOYSA-N 0.000 abstract 1
- UXUZMYHSICIOQT-UHFFFAOYSA-N 3-chloro-2,4,5,6-tetrafluoropyridine Chemical compound FC1=NC(F)=C(Cl)C(F)=C1F UXUZMYHSICIOQT-UHFFFAOYSA-N 0.000 abstract 1
- ZPPSRHQNUJAWSR-UHFFFAOYSA-N 4,5-dichloro-2,3-difluoropyridine Chemical class ClC=1C(=C(C(=NC1)F)F)Cl ZPPSRHQNUJAWSR-UHFFFAOYSA-N 0.000 abstract 1
- YZCGGIUJABHGRQ-UHFFFAOYSA-N 4-bromo-2,3,5,6-tetrafluoropyridine Chemical compound FC1=NC(F)=C(F)C(Br)=C1F YZCGGIUJABHGRQ-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000005754 fluoropyridines Chemical class 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical class [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 abstract 1
- AMQDBUIQKQUCKY-UHFFFAOYSA-M magnesium;1,2,3,4,5-pentafluorobenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].FC1=[C-]C(F)=C(F)C(F)=C1F AMQDBUIQKQUCKY-UHFFFAOYSA-M 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- 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
- C07D213/69—Two or more oxygen atoms
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1038164A GB1107881A (en) | 1964-03-11 | 1964-03-11 | Fluorinated pyridines |
| NL6503014A NL6503014A (enrdf_load_stackoverflow) | 1964-03-11 | 1965-03-09 | |
| DE1965N0026355 DE1620068A1 (de) | 1964-03-11 | 1965-03-10 | Verfahren zur Herstellung von fluorierten Pyridinderivaten |
| FR8623A FR1432872A (fr) | 1964-03-11 | 1965-03-10 | Fluoropyridines et procédé pour leur préparation |
| BE660873D BE660873A (enrdf_load_stackoverflow) | 1964-03-11 | 1965-03-10 | |
| CH341965A CH454142A (de) | 1964-03-11 | 1965-03-11 | Verfahren zur Herstellung von Fluorpyridinen und substituierten Fluorpyridinen |
| AU19164/70A AU1916470A (en) | 1964-03-11 | 1970-08-25 | Preparation of fluorinated pyridines |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1038164A GB1107881A (en) | 1964-03-11 | 1964-03-11 | Fluorinated pyridines |
| GB28065 | 1965-01-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1107881A true GB1107881A (en) | 1968-03-27 |
Family
ID=26235816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1038164A Expired GB1107881A (en) | 1964-03-11 | 1964-03-11 | Fluorinated pyridines |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU1916470A (enrdf_load_stackoverflow) |
| BE (1) | BE660873A (enrdf_load_stackoverflow) |
| CH (1) | CH454142A (enrdf_load_stackoverflow) |
| DE (1) | DE1620068A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1432872A (enrdf_load_stackoverflow) |
| GB (1) | GB1107881A (enrdf_load_stackoverflow) |
| NL (1) | NL6503014A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ299678B6 (cs) * | 1999-03-31 | 2008-10-15 | Basf Agro B.V., Arnhem (Nl), Wädenswil-Branch | Zpusob prípravy arylaminových sloucenin |
-
1964
- 1964-03-11 GB GB1038164A patent/GB1107881A/en not_active Expired
-
1965
- 1965-03-09 NL NL6503014A patent/NL6503014A/xx unknown
- 1965-03-10 BE BE660873D patent/BE660873A/xx unknown
- 1965-03-10 FR FR8623A patent/FR1432872A/fr not_active Expired
- 1965-03-10 DE DE1965N0026355 patent/DE1620068A1/de active Pending
- 1965-03-11 CH CH341965A patent/CH454142A/de unknown
-
1970
- 1970-08-25 AU AU19164/70A patent/AU1916470A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ299678B6 (cs) * | 1999-03-31 | 2008-10-15 | Basf Agro B.V., Arnhem (Nl), Wädenswil-Branch | Zpusob prípravy arylaminových sloucenin |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620068A1 (de) | 1970-05-14 |
| CH454142A (de) | 1968-04-15 |
| FR1432872A (fr) | 1966-03-25 |
| AU1916470A (en) | 1970-10-29 |
| NL6503014A (enrdf_load_stackoverflow) | 1965-09-13 |
| BE660873A (enrdf_load_stackoverflow) | 1965-07-01 |
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