PL102693B1 - Sposob wytwarzania nowych pochodnych chlorowco-2-pirolidynonu - Google Patents
Sposob wytwarzania nowych pochodnych chlorowco-2-pirolidynonu Download PDFInfo
- Publication number
- PL102693B1 PL102693B1 PL1976200412A PL20041276A PL102693B1 PL 102693 B1 PL102693 B1 PL 102693B1 PL 1976200412 A PL1976200412 A PL 1976200412A PL 20041276 A PL20041276 A PL 20041276A PL 102693 B1 PL102693 B1 PL 102693B1
- Authority
- PL
- Poland
- Prior art keywords
- chlorine
- atom
- hydrogen
- radical
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000460 chlorine Substances 0.000 claims description 145
- 229910052801 chlorine Chemical group 0.000 claims description 21
- -1 cycloalkylalkyl radical Chemical class 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 17
- 238000009835 boiling Methods 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229960002089 ferrous chloride Drugs 0.000 claims description 6
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910021575 Iron(II) bromide Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229940046149 ferrous bromide Drugs 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims 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 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910001448 ferrous ion Inorganic materials 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- AWJXEUXVDUIDEV-UHFFFAOYSA-N 1-chloropyrrolidin-2-one Chemical class ClN1CCCC1=O AWJXEUXVDUIDEV-UHFFFAOYSA-N 0.000 claims 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004803 chlorobenzyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229920005555 halobutyl Polymers 0.000 claims 1
- 125000004968 halobutyl group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229960003284 iron Drugs 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 3
- 239000000391 magnesium silicate Substances 0.000 description 3
- 229910052919 magnesium silicate Inorganic materials 0.000 description 3
- 235000019792 magnesium silicate Nutrition 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000162475 Juniperus rigida Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FEOZBZXSEJHJJL-UHFFFAOYSA-N 1-benzyl-3-chloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1CC1=CC=CC=C1 FEOZBZXSEJHJJL-UHFFFAOYSA-N 0.000 description 1
- WWINJKYFUBEFBE-UHFFFAOYSA-N 2,2-dichloro-n-prop-2-enyl-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(N(CC=C)C(=O)C(Cl)Cl)=C1 WWINJKYFUBEFBE-UHFFFAOYSA-N 0.000 description 1
- CJMUVMINGJFKIR-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;methoxymethane Chemical compound COC.OCCOCCO CJMUVMINGJFKIR-UHFFFAOYSA-N 0.000 description 1
- LFGYJPTZXAIBRJ-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(cyclopropylmethyl)pyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1CC1CC1 LFGYJPTZXAIBRJ-UHFFFAOYSA-N 0.000 description 1
- QIKAXUAIAUOSQW-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-prop-2-enylpyrrolidin-2-one Chemical compound ClCC1CN(CC=C)C(=O)C1Cl QIKAXUAIAUOSQW-UHFFFAOYSA-N 0.000 description 1
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102100023849 Glycophorin-C Human genes 0.000 description 1
- 101100229307 Homo sapiens GYPC gene Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- QACCCIVMWADWMN-UHFFFAOYSA-N ethane-1,2-diol;methoxymethane Chemical compound COC.OCCO QACCCIVMWADWMN-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000001665 trituration Methods 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56327975A | 1975-03-28 | 1975-03-28 | |
| US56328075A | 1975-03-28 | 1975-03-28 | |
| US05/647,963 US4110105A (en) | 1975-03-28 | 1976-01-09 | Aromatic N-substituted halo-substituted-2-pyrrolidinones and their utility as herbicides |
| US05/647,962 US4069038A (en) | 1975-03-28 | 1976-01-09 | Acyclic and alicyclic N-substituted halo-2-pyrrolidinones and their utility as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL102693B1 true PL102693B1 (pl) | 1979-04-30 |
Family
ID=27504836
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976200412A PL102693B1 (pl) | 1975-03-28 | 1976-03-27 | Sposob wytwarzania nowych pochodnych chlorowco-2-pirolidynonu |
| PL1976188292A PL100036B1 (pl) | 1975-03-28 | 1976-03-27 | Srodek chwastobojczy |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976188292A PL100036B1 (pl) | 1975-03-28 | 1976-03-27 | Srodek chwastobojczy |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS6011695B2 (en, 2012) |
| AU (1) | AU502662B2 (en, 2012) |
| BE (1) | BE839977A (en, 2012) |
| BG (2) | BG29122A3 (en, 2012) |
| BR (1) | BR7601774A (en, 2012) |
| CA (1) | CA1076588A (en, 2012) |
| CH (1) | CH625394A5 (en, 2012) |
| DD (1) | DD126149A5 (en, 2012) |
| DE (2) | DE2661042C2 (en, 2012) |
| DK (1) | DK145891C (en, 2012) |
| ES (1) | ES446388A1 (en, 2012) |
| FR (1) | FR2305434A1 (en, 2012) |
| GB (1) | GB1522869A (en, 2012) |
| HU (1) | HU179058B (en, 2012) |
| IL (1) | IL49289A (en, 2012) |
| IN (1) | IN143281B (en, 2012) |
| IT (1) | IT1057396B (en, 2012) |
| MX (1) | MX3355E (en, 2012) |
| MY (1) | MY8000091A (en, 2012) |
| NL (1) | NL187313C (en, 2012) |
| NZ (1) | NZ180424A (en, 2012) |
| PH (1) | PH15176A (en, 2012) |
| PL (2) | PL102693B1 (en, 2012) |
| SU (1) | SU942590A3 (en, 2012) |
| YU (1) | YU40279B (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU527254B2 (en) * | 1979-02-26 | 1983-02-24 | Stauffer Chemical Company | Synergistic herbicides |
| DE3168705D1 (en) * | 1980-12-19 | 1985-03-14 | Ciba Geigy Ag | Fluoropyrrolidinones, process for their preparation, herbicides containing them and their use |
| DK162087C (da) * | 1983-06-16 | 1992-02-24 | Stauffer Chemical Co | Fremgangsmaade til fremstilling af n-arylhalogenpyrrolidoner |
| FI74385C (fi) * | 1983-12-05 | 1988-02-08 | Stauffer Chemical Co | Synergistiska herbicidblandningar av tiokarbamat och pyrrolidonfoerening. |
| FR2589150B2 (fr) * | 1985-10-25 | 1987-11-20 | Rhone Poulenc Spec Chim | Procede de preparation de n alcene-2 yl m.trifluoromethylanilines |
| EP0205391B1 (fr) * | 1985-05-22 | 1988-10-26 | Rhone-Poulenc Chimie | Procédé de préparation de N alcène-2 yl M-trifluorométhylanilines |
| FR2582300B1 (fr) * | 1985-05-22 | 1987-07-10 | Rhone Poulenc Spec Chim | Procede de preparation de n-2 alcene-2 yl m-trifluoromethylanilines |
| FR2625197B1 (fr) * | 1987-12-23 | 1990-04-27 | Rhone Poulenc Chimie | Procede d'acylation d'une n,n-diallylaniline |
| FR2634762B1 (fr) * | 1988-07-29 | 1990-11-02 | Rhone Poulenc Chimie | Procede de preparation de n-allyl et alkyl-anilines |
| US5210305A (en) * | 1988-07-29 | 1993-05-11 | Rhone-Poulenc Chimie | Process for preparing n-alkylanilines and n-allylanilines |
| FR2634761B1 (fr) * | 1988-07-29 | 1990-11-23 | Rhone Poulenc Chimie | Procede de preparation de n-allyl et de n-alkylanilines |
| US5189220A (en) * | 1988-07-29 | 1993-02-23 | Rhone-Poulenc Chimie | Process for preparing N-alkylanilines and N-allylanilines catalyzed by iodides |
| FR2643902B1 (fr) * | 1989-03-03 | 1991-10-11 | Rhone Poulenc Chimie | Procede de preparation de n-allylmetatrifluoromethylaniline |
| JPH02237970A (ja) * | 1989-03-13 | 1990-09-20 | Mitsui Toatsu Chem Inc | ４―エチル―１―（３―トリフルオロメチルフェニル）―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 |
| FR2663927A1 (fr) * | 1989-06-05 | 1992-01-03 | Rhone Poulenc Chimie | Procede de preparation de n monoalkyl- ou alkenylanilines. |
| 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 |
| ATE160140T1 (de) * | 1990-08-02 | 1997-11-15 | Rhone Poulenc Chimie | Allylierungsreagens und ein es verwendendes herstellungsverfahren |
| FR2665439B1 (fr) * | 1990-08-02 | 1992-11-06 | Rhone Poulenc Chimie | Reactif de n-allylation et procede de synthese d'une n acyl, n allylaniline. |
| US5538985A (en) * | 1994-01-27 | 1996-07-23 | Mitsui Toatsu Chemicals, Inc. | Pyrrolidinone derivatives |
| EP2052612A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037629A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN114031536A (zh) * | 2021-12-14 | 2022-02-11 | 青海省农林科学院 | 一种抑制杂草种子萌发及幼苗生长的纯光学异构体化合物及应用 |
| AR129510A1 (es) | 2022-06-03 | 2024-09-04 | Adama Agan Ltd | Nuevas mezclas para la protección de cultivos |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49134835A (en, 2012) * | 1973-05-08 | 1974-12-25 |
-
1976
- 1976-03-17 HU HU76SA2904A patent/HU179058B/hu unknown
- 1976-03-17 FR FR7607683A patent/FR2305434A1/fr active Granted
- 1976-03-19 JP JP51030778A patent/JPS6011695B2/ja not_active Expired
- 1976-03-23 BR BR7601774A patent/BR7601774A/pt unknown
- 1976-03-23 IN IN510/CAL/1976A patent/IN143281B/en unknown
- 1976-03-23 GB GB11627/76A patent/GB1522869A/en not_active Expired
- 1976-03-24 MX MX000109U patent/MX3355E/es unknown
- 1976-03-24 BE BE7000801A patent/BE839977A/xx not_active IP Right Cessation
- 1976-03-24 PH PH18252A patent/PH15176A/en unknown
- 1976-03-24 CH CH368776A patent/CH625394A5/de not_active IP Right Cessation
- 1976-03-25 DD DD192041A patent/DD126149A5/xx unknown
- 1976-03-25 DE DE2661042A patent/DE2661042C2/de not_active Expired
- 1976-03-25 IL IL49289A patent/IL49289A/xx unknown
- 1976-03-25 BG BG032702A patent/BG29122A3/xx unknown
- 1976-03-25 DE DE2612731A patent/DE2612731C2/de not_active Expired
- 1976-03-25 BG BG033675A patent/BG29135A3/xx unknown
- 1976-03-25 NZ NZ180424A patent/NZ180424A/xx unknown
- 1976-03-26 NL NLAANVRAGE7603193,A patent/NL187313C/xx not_active IP Right Cessation
- 1976-03-26 ES ES446388A patent/ES446388A1/es not_active Expired
- 1976-03-26 IT IT48736/76A patent/IT1057396B/it active
- 1976-03-26 CA CA248,947A patent/CA1076588A/en not_active Expired
- 1976-03-26 YU YU800/76A patent/YU40279B/xx unknown
- 1976-03-26 AU AU12413/76A patent/AU502662B2/en not_active Expired
- 1976-03-26 DK DK135776A patent/DK145891C/da not_active IP Right Cessation
- 1976-03-27 PL PL1976200412A patent/PL102693B1/pl unknown
- 1976-03-27 PL PL1976188292A patent/PL100036B1/pl unknown
- 1976-11-23 SU SU762421801A patent/SU942590A3/ru active
-
1980
- 1980-12-30 MY MY91/80A patent/MY8000091A/xx unknown
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