DE1668626A1 - Verfahren zur Herstellung organischer Verbindungen aus monomeren Iminen - Google Patents
Verfahren zur Herstellung organischer Verbindungen aus monomeren IminenInfo
- Publication number
- DE1668626A1 DE1668626A1 DE19671668626 DE1668626A DE1668626A1 DE 1668626 A1 DE1668626 A1 DE 1668626A1 DE 19671668626 DE19671668626 DE 19671668626 DE 1668626 A DE1668626 A DE 1668626A DE 1668626 A1 DE1668626 A1 DE 1668626A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- cycloalkyl
- imine
- monomeric
- 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.)
- Granted
Links
- 150000002466 imines Chemical class 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 12
- 150000002894 organic compounds Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- -1 nickel peroxide Chemical class 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 14
- 230000009102 absorption Effects 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 239000010779 crude oil Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- 150000004705 aldimines Chemical class 0.000 description 4
- 150000001793 charged compounds Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
- MFGOZCIHXVFZBC-UHFFFAOYSA-N 1-propylpyrrole Chemical compound CCCN1C=CC=C1 MFGOZCIHXVFZBC-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- IILLGPHWDHXXRH-UHFFFAOYSA-N 3,4-diethyl-1-(2-methylpropyl)pyrrole Chemical compound C(C(C)C)N1C=C(C(=C1)CC)CC IILLGPHWDHXXRH-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 102100021757 E3 ubiquitin-protein ligase RNF135 Human genes 0.000 description 1
- 101001106984 Homo sapiens E3 ubiquitin-protein ligase RNF135 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- QCVHZXIQEDRLSM-UHFFFAOYSA-N N-(2-methylpropyl)pentan-2-imine Chemical compound CC(CCC)=NCC(C)C QCVHZXIQEDRLSM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 1
- PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- YSWBBDGSRZJBIO-UHFFFAOYSA-N n-butylpentan-2-imine Chemical compound CCCCN=C(C)CCC YSWBBDGSRZJBIO-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59500166A | 1966-11-17 | 1966-11-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1668626A1 true DE1668626A1 (de) | 1971-07-29 |
| DE1668626B2 DE1668626B2 (enExample) | 1974-01-10 |
| DE1668626C3 DE1668626C3 (enExample) | 1974-08-01 |
Family
ID=24381292
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671795618 Pending DE1795618A1 (de) | 1966-11-17 | 1967-11-14 | Verfahren zur Herstellung von Pyrolen |
| DE19671668626 Granted DE1668626A1 (de) | 1966-11-17 | 1967-11-14 | Verfahren zur Herstellung organischer Verbindungen aus monomeren Iminen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671795618 Pending DE1795618A1 (de) | 1966-11-17 | 1967-11-14 | Verfahren zur Herstellung von Pyrolen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE706725A (enExample) |
| CH (1) | CH540884A (enExample) |
| DE (2) | DE1795618A1 (enExample) |
| GB (1) | GB1177160A (enExample) |
| NL (1) | NL6715507A (enExample) |
-
1967
- 1967-10-24 GB GB4838567A patent/GB1177160A/en not_active Expired
- 1967-11-14 DE DE19671795618 patent/DE1795618A1/de active Pending
- 1967-11-14 DE DE19671668626 patent/DE1668626A1/de active Granted
- 1967-11-15 NL NL6715507A patent/NL6715507A/xx unknown
- 1967-11-16 CH CH1602867A patent/CH540884A/de not_active IP Right Cessation
- 1967-11-17 BE BE706725D patent/BE706725A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1177160A (en) | 1970-01-07 |
| BE706725A (enExample) | 1968-05-17 |
| DE1668626C3 (enExample) | 1974-08-01 |
| CH540884A (de) | 1973-08-31 |
| DE1795618A1 (de) | 1972-04-06 |
| DE1668626B2 (enExample) | 1974-01-10 |
| NL6715507A (enExample) | 1968-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE851496C (de) | Verfahren zur Herstellung symmetrischer oder unsymmetrischer aliphatischer, ditertiaerer Peroxyde | |
| DE2315640C3 (de) | Verfahren zur Herstellung ungesättigter cycloaliphatischer Ketone und dabei gebildete cycloaliphatische Diketone und deren Enolate | |
| EP0008096A2 (de) | Verfahren zur Herstellung von 2-(Perfluoralkyl)-äthanolen | |
| DE3744094A1 (de) | Verfahren zur herstellung von cyclischen ketonen durch isomerisierung von epoxiden | |
| DE4303647A1 (de) | Cyclopentadiene mit funktionalisierter Kohlenwasserstoff-Seitenkette | |
| DE1668626A1 (de) | Verfahren zur Herstellung organischer Verbindungen aus monomeren Iminen | |
| DE2106768B2 (de) | Komplexverbindungen aus Organonatriumverbindungen und Chelate bildenden Polyaminen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Telomerisationskatalysatoren und zur Reinigung von Organonatriumverbindungen | |
| DE1593466A1 (de) | Herstellung von Aldehyden und/oder Alkoholen | |
| DE2329923C3 (de) | Verfahren zur Herstellung von 5-Oxohexannitri! | |
| DE69607568T2 (de) | Verfahren zur Herstellung von Additionsprodukten aus Aminen und Alpha-Beta ungesättigten Verbindungen | |
| DE2430287A1 (de) | Verfahren zur herstellung von ungesaettigten alkoholen | |
| DE2331675C2 (de) | Verfahren zur Herstellung von aliphatischen Ketenacetalen | |
| DE3106169A1 (de) | Verfahren zur herstellung eines 3.3.3.-trifluorpropylierten benzolderivats | |
| EP0525579B1 (de) | Verfahren zur Herstellung von substituierten Hexensäuren | |
| EP0606058A2 (de) | Halogenierte Zimtsäuren und deren Ester, sowie Verfahren zu ihrer Herstellung und halogenierte Aryldiazoniumsalze | |
| DE2854627B1 (de) | Verfahren zur Herstellung von Aminocarbonsaeruehydrochloriden bzw. Diaminocarbonsaeure-di-hydrochloriden | |
| DE2741632A1 (de) | Verfahren zur herstellung von carbonylverbindungen | |
| DE2005515B2 (de) | Verfahren zur Herstellung von γ -Cyanburyraldiminen | |
| DE2141406A1 (de) | Verfahren zur Herstellung von Triarylmethanen | |
| DE2653646C2 (de) | Substituierte Propargylalkohole | |
| AT358059B (de) | Verfahren zur herstellung von neuen oxiranen | |
| DE2346201C2 (de) | Verfahren zur Herstellung von ω-Cyan-derivaten von β-Alkoxycarbonsäureestern | |
| DE2026043A1 (enExample) | ||
| DE69310136T2 (de) | Aliphatische Omega-hydroxy-3-ketonitrile und Verfahren zur Herstellung von aliphatischen Omega-hydroxycarbonsäuren | |
| AT354457B (de) | Verfahren zur herstellung von neuen 0-(2,3- epoxypropyl)-hydroximsaeureestern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |