DE1445463A1 - Verfahren zur Herstellung von heterocyclischen organischen Verbindungen - Google Patents
Verfahren zur Herstellung von heterocyclischen organischen VerbindungenInfo
- Publication number
- DE1445463A1 DE1445463A1 DE19641445463 DE1445463A DE1445463A1 DE 1445463 A1 DE1445463 A1 DE 1445463A1 DE 19641445463 DE19641445463 DE 19641445463 DE 1445463 A DE1445463 A DE 1445463A DE 1445463 A1 DE1445463 A1 DE 1445463A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- substituted
- parts
- pyrrole
- weight
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 39
- -1 heterocyclic organic compounds Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 24
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 150000003233 pyrroles Chemical class 0.000 claims description 9
- 229940123973 Oxygen scavenger Drugs 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 229910001882 dioxygen Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- CVZGUJMLZZTPKH-UHFFFAOYSA-N octane-3,6-dione Chemical compound CCC(=O)CCC(=O)CC CVZGUJMLZZTPKH-UHFFFAOYSA-N 0.000 claims description 6
- IRTLROCMFSDSNF-UHFFFAOYSA-N 2-phenyl-1h-pyrrole Chemical compound C1=CNC(C=2C=CC=CC=2)=C1 IRTLROCMFSDSNF-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 4
- XDXPOGUNVDBTHC-UHFFFAOYSA-N 2-ethyl-5-phenyl-1h-pyrrole Chemical compound N1C(CC)=CC=C1C1=CC=CC=C1 XDXPOGUNVDBTHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- VWHNHZCURHSPOX-UHFFFAOYSA-N 2-phenyl-5-propan-2-yl-1h-pyrrole Chemical compound N1C(C(C)C)=CC=C1C1=CC=CC=C1 VWHNHZCURHSPOX-UHFFFAOYSA-N 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 150000002518 isoindoles Chemical class 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
- PQOLSXITALXRKK-UHFFFAOYSA-N 2,5-bis(2-methylphenyl)-1H-pyrrole Chemical compound C1(=C(C=CC=C1)C=1NC(=CC1)C1=C(C=CC=C1)C)C PQOLSXITALXRKK-UHFFFAOYSA-N 0.000 claims 1
- RYXXWPBMCRQHNB-UHFFFAOYSA-N 2,5-dipropyl-1h-pyrrole Chemical compound CCCC1=CC=C(CCC)N1 RYXXWPBMCRQHNB-UHFFFAOYSA-N 0.000 claims 1
- QCXXRGFMOVLAQY-UHFFFAOYSA-N 2-(2-methylphenyl)-5-phenyl-1H-pyrrole Chemical compound C1(=CC=CC=C1)C=1NC(=CC1)C1=C(C=CC=C1)C QCXXRGFMOVLAQY-UHFFFAOYSA-N 0.000 claims 1
- LGSFUHPSKVXCMP-UHFFFAOYSA-N 2-ethyl-5-propan-2-yl-1h-pyrrole Chemical compound CCC1=CC=C(C(C)C)N1 LGSFUHPSKVXCMP-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- HGRGPAAXHOTBAM-UHFFFAOYSA-N Heptan-2,5-dione Chemical compound CCC(=O)CCC(C)=O HGRGPAAXHOTBAM-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 238000005476 soldering Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000013078 crystal Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- RJCRXUOYULQDPG-UHFFFAOYSA-N 2,5-diphenyl-1h-pyrrole Chemical compound C=1C=C(C=2C=CC=CC=2)NC=1C1=CC=CC=C1 RJCRXUOYULQDPG-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229940075930 picrate Drugs 0.000 description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- CIKZQBMEPDKJHF-UHFFFAOYSA-N 2,5-diethyl-1h-pyrrole Chemical compound CCC1=CC=C(CC)N1 CIKZQBMEPDKJHF-UHFFFAOYSA-N 0.000 description 2
- ONGBXISBKSVVFS-UHFFFAOYSA-N 2-methyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)C(=O)C1=CC=CC=C1 ONGBXISBKSVVFS-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- YBHPWRGGYIDPLJ-UHFFFAOYSA-N 1,3,4,7-tetraphenyl-2H-isoindole Chemical compound C1(=CC=CC=C1)C=1NC(=C2C(=CC=C(C12)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 YBHPWRGGYIDPLJ-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- GUZANAKOJHDQAH-UHFFFAOYSA-N 2-ethyl-5-(4-methylphenyl)-1H-pyrrole Chemical compound C(C)C=1NC(=CC1)C1=CC=C(C=C1)C GUZANAKOJHDQAH-UHFFFAOYSA-N 0.000 description 1
- LOLZVJJIBIGCFD-UHFFFAOYSA-N 2-methyl-5-phenyl-1h-pyrrole Chemical compound N1C(C)=CC=C1C1=CC=CC=C1 LOLZVJJIBIGCFD-UHFFFAOYSA-N 0.000 description 1
- VJHOGOXWXLEMQZ-UHFFFAOYSA-N 2-methyl-5-propyl-1h-pyrrole Chemical compound CCCC1=CC=C(C)N1 VJHOGOXWXLEMQZ-UHFFFAOYSA-N 0.000 description 1
- YYUISDWOKJLVMA-UHFFFAOYSA-N 2-propan-2-yl-1h-pyrrole Chemical compound CC(C)C1=CC=CN1 YYUISDWOKJLVMA-UHFFFAOYSA-N 0.000 description 1
- MJBDTJMEQIKGAO-UHFFFAOYSA-N 4,7-dimethyl-1,3-diphenyl-2h-isoindole Chemical compound C=12C(C)=CC=C(C)C2=C(C=2C=CC=CC=2)NC=1C1=CC=CC=C1 MJBDTJMEQIKGAO-UHFFFAOYSA-N 0.000 description 1
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 1
- 101150111329 ACE-1 gene Proteins 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SPDFSSLYVRCMDZ-UHFFFAOYSA-N octane-2,5-dione Chemical compound CCCC(=O)CCC(C)=O SPDFSSLYVRCMDZ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/20—Treatment of water, waste water, or sewage by degassing, i.e. liberation of dissolved gases
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Water Supply & Treatment (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4554863 | 1963-11-19 | ||
| GB4554963 | 1963-11-19 | ||
| GB4555063 | 1963-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445463A1 true DE1445463A1 (de) | 1968-11-21 |
Family
ID=27259894
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641445463 Pending DE1445463A1 (de) | 1963-11-19 | 1964-11-19 | Verfahren zur Herstellung von heterocyclischen organischen Verbindungen |
| DE19641445470 Pending DE1445470A1 (de) | 1963-11-19 | 1964-11-19 | Verfahren zur Herstellung von heterocyclischen organischen Verbindungen |
| DE19641445464 Pending DE1445464A1 (de) | 1963-11-19 | 1964-11-19 | Verfahren zur Herstellung von heterocyclischen organischen Verbindungen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641445470 Pending DE1445470A1 (de) | 1963-11-19 | 1964-11-19 | Verfahren zur Herstellung von heterocyclischen organischen Verbindungen |
| DE19641445464 Pending DE1445464A1 (de) | 1963-11-19 | 1964-11-19 | Verfahren zur Herstellung von heterocyclischen organischen Verbindungen |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US3322785A (forum.php) |
| BE (3) | BE655869A (forum.php) |
| CH (3) | CH454856A (forum.php) |
| DE (3) | DE1445463A1 (forum.php) |
| GB (3) | GB1051915A (forum.php) |
| IT (1) | IT1044773B (forum.php) |
| NL (5) | NL6413422A (forum.php) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4363734A (en) * | 1981-02-05 | 1982-12-14 | Nalco Chemical Company | 1,3-Dihydroxy acetone as an oxygen scavenger for water |
| US5200427A (en) * | 1984-07-27 | 1993-04-06 | The Board Of Trustees Of The Univ. Of Illinois | Porphyric insecticides |
| RU2185391C1 (ru) * | 2001-01-03 | 2002-07-20 | Бондалетов Владимир Григорьевич | Способ получения пленкообразующего |
| EP2754690B1 (en) | 2007-05-10 | 2017-12-13 | Plastipak Packaging, Inc. | Oxygen scavenging molecules, articles containing same, and methods of their use |
| WO2011043969A2 (en) | 2009-09-29 | 2011-04-14 | Constar International | Colorant compatible oxygen scavenging polymer compositions and articles made from same |
| US8450398B2 (en) | 2009-11-13 | 2013-05-28 | Constar International, Inc. | Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions |
| EP2499195B1 (en) * | 2009-11-13 | 2020-12-09 | Plastipak Packaging, Inc. | Oxygen scavengers, compositions comprising the scavengers, and artcles made from the compositions |
| CN104379654A (zh) | 2012-04-30 | 2015-02-25 | 普莱斯提派克包装公司 | 除氧组合物 |
| US11338983B2 (en) | 2014-08-22 | 2022-05-24 | Plastipak Packaging, Inc. | Oxygen scavenging compositions, articles containing same, and methods of their use |
| US10351692B2 (en) | 2014-10-17 | 2019-07-16 | Plastipak Packaging, Inc. | Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3007939A (en) * | 1959-03-23 | 1961-11-07 | Dow Chemical Co | N-substituted isoindoles |
-
0
- NL NL126384D patent/NL126384C/xx active
- GB GB1051917D patent/GB1051917A/en active Active
- GB GB1051916D patent/GB1051916A/en active Active
- NL NL127609D patent/NL127609C/xx active
- GB GB1051915D patent/GB1051915A/en active Active
-
1964
- 1964-11-09 IT IT23927/64A patent/IT1044773B/it active
- 1964-11-13 CH CH1466164A patent/CH454856A/de unknown
- 1964-11-16 CH CH1474664A patent/CH458349A/de unknown
- 1964-11-16 US US411597A patent/US3322785A/en not_active Expired - Lifetime
- 1964-11-17 BE BE655869D patent/BE655869A/xx unknown
- 1964-11-17 BE BE655868D patent/BE655868A/xx unknown
- 1964-11-18 NL NL6413422A patent/NL6413422A/xx unknown
- 1964-11-18 NL NL6413420A patent/NL6413420A/xx unknown
- 1964-11-18 BE BE655919D patent/BE655919A/xx unknown
- 1964-11-18 NL NL6413421A patent/NL6413421A/xx unknown
- 1964-11-18 CH CH1484864A patent/CH463506A/de unknown
- 1964-11-19 DE DE19641445463 patent/DE1445463A1/de active Pending
- 1964-11-19 DE DE19641445470 patent/DE1445470A1/de active Pending
- 1964-11-19 DE DE19641445464 patent/DE1445464A1/de active Pending
-
1967
- 1967-01-20 US US627575A patent/US3448119A/en not_active Expired - Lifetime
- 1967-01-20 US US627576A patent/US3441571A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL6413420A (forum.php) | 1965-05-20 |
| NL126384C (forum.php) | |
| CH454856A (de) | 1968-04-30 |
| NL6413421A (forum.php) | 1965-05-20 |
| US3441571A (en) | 1969-04-29 |
| BE655919A (forum.php) | 1965-05-18 |
| US3448119A (en) | 1969-06-03 |
| GB1051915A (forum.php) | |
| BE655868A (forum.php) | 1965-05-17 |
| DE1445470A1 (de) | 1969-03-13 |
| DE1445464A1 (de) | 1969-02-06 |
| IT1044773B (it) | 1980-04-21 |
| BE655869A (forum.php) | 1965-05-17 |
| GB1051917A (forum.php) | |
| GB1051916A (forum.php) | |
| NL127609C (forum.php) | |
| CH463506A (de) | 1968-10-15 |
| NL6413422A (forum.php) | 1965-05-20 |
| US3322785A (en) | 1967-05-30 |
| CH458349A (de) | 1968-06-30 |
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