DD224317A5 - Verfahren zur herstellung von n-arylhalo-pyrrolidonen - Google Patents
Verfahren zur herstellung von n-arylhalo-pyrrolidonen Download PDFInfo
- Publication number
- DD224317A5 DD224317A5 DD84264189A DD26418984A DD224317A5 DD 224317 A5 DD224317 A5 DD 224317A5 DD 84264189 A DD84264189 A DD 84264189A DD 26418984 A DD26418984 A DD 26418984A DD 224317 A5 DD224317 A5 DD 224317A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- copper
- reaction
- catalyst
- amine
- amines
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 238000000034 method Methods 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 abstract description 25
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052802 copper Inorganic materials 0.000 abstract description 16
- 239000010949 copper Substances 0.000 abstract description 16
- 150000005619 secondary aliphatic amines Chemical class 0.000 abstract description 3
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
- 239000002904 solvent Substances 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000000460 chlorine Chemical group 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 13
- 150000002431 hydrogen Chemical group 0.000 description 13
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011269 tar Substances 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 229910052731 fluorine Chemical group 0.000 description 7
- 239000011737 fluorine Chemical group 0.000 description 7
- 150000003335 secondary amines Chemical class 0.000 description 7
- 229960001413 acetanilide Drugs 0.000 description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical group CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- -1 trifluoromethylsulfinyl Chemical group 0.000 description 4
- 239000005749 Copper compound Substances 0.000 description 3
- 150000001880 copper compounds Chemical class 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KQTOYEUYHXUEDB-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanamide Chemical compound NC(=O)C(F)(F)C(F)(F)F KQTOYEUYHXUEDB-UHFFFAOYSA-N 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 229960004643 cupric oxide Drugs 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical group FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical group NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical group CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [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
- HMMPCBAWTWYFLR-UHFFFAOYSA-N n-pyridin-2-ylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=N1 HMMPCBAWTWYFLR-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006308 propyl amino group Chemical class 0.000 description 1
- 229910052707 ruthenium Inorganic materials 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Saccharide Compounds (AREA)
- Pyridine Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
- Fishing Rods (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50513583A | 1983-06-16 | 1983-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD224317A5 true DD224317A5 (de) | 1985-07-03 |
Family
ID=24009165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84264189A DD224317A5 (de) | 1983-06-16 | 1984-06-15 | Verfahren zur herstellung von n-arylhalo-pyrrolidonen |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0129296B1 (cs) |
| JP (1) | JPS6011464A (cs) |
| KR (1) | KR890004126B1 (cs) |
| AT (1) | ATE32062T1 (cs) |
| AU (1) | AU563172B2 (cs) |
| BG (1) | BG49382A3 (cs) |
| BR (1) | BR8402873A (cs) |
| CA (1) | CA1216298A (cs) |
| CS (1) | CS241090B2 (cs) |
| DD (1) | DD224317A5 (cs) |
| DE (1) | DE3468864D1 (cs) |
| DK (1) | DK162087C (cs) |
| DZ (1) | DZ648A1 (cs) |
| EG (1) | EG20053A (cs) |
| ES (1) | ES533471A0 (cs) |
| HU (1) | HU192034B (cs) |
| IL (1) | IL72110A (cs) |
| MA (1) | MA20147A1 (cs) |
| MX (1) | MX156039A (cs) |
| NZ (1) | NZ208537A (cs) |
| PL (1) | PL142334B1 (cs) |
| PT (1) | PT78747B (cs) |
| RO (1) | RO88419A (cs) |
| SU (1) | SU1452479A3 (cs) |
| TR (1) | TR22866A (cs) |
| YU (1) | YU44565B (cs) |
| ZA (1) | ZA844532B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2728937B2 (ja) * | 1989-06-14 | 1998-03-18 | 三井東圧化学株式会社 | １―（３―置換ベンジル）―３―ハロゲノ―４―（１―ハロゲノアルキル）―２―ピロリジノン誘導体およびこれらを有効成分とする除草剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2305434A1 (fr) * | 1975-03-28 | 1976-10-22 | Stauffer Chemical Co | Procede de preparation pour l'emploi en tant qu'herbicides d'halo-2-pyrrolidinones n-substituees, de types acycliques, alicycliques, monocycliques, aromatiques ou phenyliques |
| US4132713A (en) * | 1977-12-23 | 1979-01-02 | Stauffer Chemical Company | Process for the preparation of N-substituted halopyrrolidones |
| EP0055215B1 (de) * | 1980-12-19 | 1985-01-30 | Ciba-Geigy Ag | Neue Fluorpyrrolidinone, Verfahren zu deren Herstellung, sie enthaltende herbizide Mittel und deren Verwendung |
-
1984
- 1984-05-29 DK DK265184A patent/DK162087C/da not_active IP Right Cessation
- 1984-06-11 YU YU1021/84A patent/YU44565B/xx unknown
- 1984-06-11 RO RO84114824A patent/RO88419A/ro unknown
- 1984-06-13 BG BG065842A patent/BG49382A3/xx unknown
- 1984-06-13 TR TR4175/84A patent/TR22866A/xx unknown
- 1984-06-13 CS CS844462A patent/CS241090B2/cs unknown
- 1984-06-13 EG EG635584A patent/EG20053A/xx active
- 1984-06-13 DZ DZ847198A patent/DZ648A1/fr active
- 1984-06-13 BR BR8402873A patent/BR8402873A/pt not_active IP Right Cessation
- 1984-06-14 AT AT84200860T patent/ATE32062T1/de not_active IP Right Cessation
- 1984-06-14 DE DE8484200860T patent/DE3468864D1/de not_active Expired
- 1984-06-14 EP EP84200860A patent/EP0129296B1/en not_active Expired
- 1984-06-14 PL PL1984248201A patent/PL142334B1/pl unknown
- 1984-06-14 IL IL72110A patent/IL72110A/xx unknown
- 1984-06-15 MX MX201673A patent/MX156039A/es unknown
- 1984-06-15 AU AU29429/84A patent/AU563172B2/en not_active Ceased
- 1984-06-15 DD DD84264189A patent/DD224317A5/de not_active IP Right Cessation
- 1984-06-15 SU SU3753761A patent/SU1452479A3/ru active
- 1984-06-15 HU HU842318A patent/HU192034B/hu not_active IP Right Cessation
- 1984-06-15 ZA ZA844532A patent/ZA844532B/xx unknown
- 1984-06-15 ES ES533471A patent/ES533471A0/es active Granted
- 1984-06-15 CA CA000456705A patent/CA1216298A/en not_active Expired
- 1984-06-15 NZ NZ208537A patent/NZ208537A/en unknown
- 1984-06-15 PT PT78747A patent/PT78747B/pt unknown
- 1984-06-15 KR KR1019840003367A patent/KR890004126B1/ko not_active Expired
- 1984-06-16 JP JP59122964A patent/JPS6011464A/ja active Granted
- 1984-06-21 MA MA20371A patent/MA20147A1/fr unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |