CH521970A - Verfahren zur Herstellung von neuen Mono- und Dialkoholen N-heterocyclischer Verbindungen - Google Patents
Verfahren zur Herstellung von neuen Mono- und Dialkoholen N-heterocyclischer VerbindungenInfo
- Publication number
- CH521970A CH521970A CH1673870A CH1673870A CH521970A CH 521970 A CH521970 A CH 521970A CH 1673870 A CH1673870 A CH 1673870A CH 1673870 A CH1673870 A CH 1673870A CH 521970 A CH521970 A CH 521970A
- Authority
- CH
- Switzerland
- Prior art keywords
- heterocyclic compound
- compound used
- dependent
- heterocyclic
- formula
- Prior art date
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 26
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 claims description 6
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 6
- VSJRBQDMBFFHMC-UHFFFAOYSA-N 5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound CCC1(C)NC(=O)NC1=O VSJRBQDMBFFHMC-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- IZEUNSNECKZMNL-UHFFFAOYSA-N 5,5-dimethyl-6-propan-2-yl-1,3-diazinane-2,4-dione Chemical compound CC(C)C1NC(=O)NC(=O)C1(C)C IZEUNSNECKZMNL-UHFFFAOYSA-N 0.000 claims description 3
- PBNUQCWZHRMSMS-UHFFFAOYSA-N 5-propan-2-ylimidazolidine-2,4-dione Chemical compound CC(C)C1NC(=O)NC1=O PBNUQCWZHRMSMS-UHFFFAOYSA-N 0.000 claims description 3
- SHVCSCWHWMSGTE-UHFFFAOYSA-N 6-methyluracil Chemical compound CC1=CC(=O)NC(=O)N1 SHVCSCWHWMSGTE-UHFFFAOYSA-N 0.000 claims description 3
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 claims description 3
- GWTZZUPJEUZZLU-UHFFFAOYSA-N 5,5-diethylimidazolidine-2,4-dione Chemical compound CCC1(CC)NC(=O)NC1=O GWTZZUPJEUZZLU-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 239000003822 epoxy resin Substances 0.000 abstract 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 2
- 229920000647 polyepoxide Polymers 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- 239000000047 product Substances 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- -1 alkyl radical Chemical class 0.000 description 13
- 238000003756 stirring Methods 0.000 description 10
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HKQNNDBSFWUIAE-UHFFFAOYSA-N 3-(2-hydroxypropyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC(O)CN1C(=O)NC(C)(C)C1=O HKQNNDBSFWUIAE-UHFFFAOYSA-N 0.000 description 4
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011346 highly viscous material Substances 0.000 description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 3
- 229940091173 hydantoin Drugs 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- HTKIZIQFMHVTRJ-UHFFFAOYSA-N 5-butyl-1,3-diazinane-2,4,6-trione Chemical compound CCCCC1C(=O)NC(=O)NC1=O HTKIZIQFMHVTRJ-UHFFFAOYSA-N 0.000 description 2
- VMAQYKGITHDWKL-UHFFFAOYSA-N 5-methylimidazolidine-2,4-dione Chemical compound CC1NC(=O)NC1=O VMAQYKGITHDWKL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical compound CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KVQUADFBNUQFNX-UHFFFAOYSA-N 1,3-bis(2-hydroxypropyl)-5-propan-2-ylimidazolidine-2,4-dione Chemical compound CC(C)C1N(CC(C)O)C(=O)N(CC(C)O)C1=O KVQUADFBNUQFNX-UHFFFAOYSA-N 0.000 description 1
- JTTFXYHJDZZDQK-UHFFFAOYSA-N 1,3-diazaspiro[4.4]nonane-2,4-dione Chemical compound N1C(=O)NC(=O)C11CCCC1 JTTFXYHJDZZDQK-UHFFFAOYSA-N 0.000 description 1
- NERNEXMEYQFFHU-UHFFFAOYSA-N 1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound N1C(=O)NC(=O)C11CCCCC1 NERNEXMEYQFFHU-UHFFFAOYSA-N 0.000 description 1
- QZIKCHYLJQUWPS-UHFFFAOYSA-N 5,5-dimethyl-1,3-diazinane-2,4-dione Chemical compound CC1(C)CNC(=O)NC1=O.CC1(C)CNC(=O)NC1=O QZIKCHYLJQUWPS-UHFFFAOYSA-N 0.000 description 1
- FMTLDVACNZDTQL-UHFFFAOYSA-N 5-ethyl-1,3-diazinane-2,4,6-trione Chemical compound CCC1C(=O)NC(=O)NC1=O FMTLDVACNZDTQL-UHFFFAOYSA-N 0.000 description 1
- QSELDKYOARDOCZ-UHFFFAOYSA-N 5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound CCCC(C)C1C(=O)NC(=O)NC1=O QSELDKYOARDOCZ-UHFFFAOYSA-N 0.000 description 1
- BIFASJFFCIDWDC-UHFFFAOYSA-N 5-propylimidazolidine-2,4-dione Chemical compound CCCC1NC(=O)NC1=O BIFASJFFCIDWDC-UHFFFAOYSA-N 0.000 description 1
- FDQGNLOWMMVRQL-UHFFFAOYSA-N Allobarbital Chemical compound C=CCC1(CC=C)C(=O)NC(=O)NC1=O FDQGNLOWMMVRQL-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- PZGLLMKGHLWTDR-UHFFFAOYSA-N CC(C)C1NC(=O)NC(=O)C1(C)C.CC(C)C1NC(=O)NC(=O)C1(C)C Chemical compound CC(C)C1NC(=O)NC(=O)C1(C)C.CC(C)C1NC(=O)NC(=O)C1(C)C PZGLLMKGHLWTDR-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- UORJNBVJVRLXMQ-UHFFFAOYSA-N aprobarbital Chemical compound C=CCC1(C(C)C)C(=O)NC(=O)NC1=O UORJNBVJVRLXMQ-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- STDBAQMTJLUMFW-UHFFFAOYSA-N butobarbital Chemical compound CCCCC1(CC)C(=O)NC(=O)NC1=O STDBAQMTJLUMFW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002924 oxiranes Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds heterocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Resins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1673870A CH521970A (de) | 1968-11-11 | 1968-11-11 | Verfahren zur Herstellung von neuen Mono- und Dialkoholen N-heterocyclischer Verbindungen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1673870A CH521970A (de) | 1968-11-11 | 1968-11-11 | Verfahren zur Herstellung von neuen Mono- und Dialkoholen N-heterocyclischer Verbindungen |
| CH1680368A CH523278A (de) | 1968-11-11 | 1968-11-11 | Verfahren zur Herstellung von neuen Diglycidyläthern von N-heterocyclischen Verbindungen und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH521970A true CH521970A (de) | 1972-04-30 |
Family
ID=4420349
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1673870A CH521970A (de) | 1968-11-11 | 1968-11-11 | Verfahren zur Herstellung von neuen Mono- und Dialkoholen N-heterocyclischer Verbindungen |
| CH76472A CH525894A (de) | 1968-11-11 | 1968-11-11 | Verfahren zur Herstellung von neuen Dialkoholen N-heterocyclischer Verbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH76472A CH525894A (de) | 1968-11-11 | 1968-11-11 | Verfahren zur Herstellung von neuen Dialkoholen N-heterocyclischer Verbindungen |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS5034031B1 (enrdf_load_stackoverflow) |
| BR (1) | BR6914069D0 (enrdf_load_stackoverflow) |
| CH (2) | CH521970A (enrdf_load_stackoverflow) |
| CS (2) | CS160116B2 (enrdf_load_stackoverflow) |
| ES (2) | ES385362A1 (enrdf_load_stackoverflow) |
| SE (1) | SE359544B (enrdf_load_stackoverflow) |
| SU (1) | SU398028A3 (enrdf_load_stackoverflow) |
| YU (1) | YU34126B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016175668A1 (en) | 2015-04-28 | 2016-11-03 | Politechnika Rzeszowska | Preparation method for 1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione and 1-phenyl-2,6-bis(2-hydroxypropyl)imidazo[1,5-c]quinazoline-3,5-dione |
-
1968
- 1968-11-11 CH CH1673870A patent/CH521970A/de not_active IP Right Cessation
- 1968-11-11 CH CH76472A patent/CH525894A/de not_active IP Right Cessation
-
1969
- 1969-11-10 SU SU1375818A patent/SU398028A3/ru active
- 1969-11-10 SE SE15377/69A patent/SE359544B/xx unknown
- 1969-11-11 CS CS6890A patent/CS160116B2/cs unknown
- 1969-11-11 JP JP44089839A patent/JPS5034031B1/ja active Pending
- 1969-11-11 CS CS7426A patent/CS160115B2/cs unknown
- 1969-11-11 BR BR214069/69A patent/BR6914069D0/pt unknown
-
1970
- 1970-10-05 YU YU2450/70A patent/YU34126B/xx unknown
- 1970-10-26 JP JP45093892A patent/JPS5034032B1/ja active Pending
- 1970-11-09 ES ES385362A patent/ES385362A1/es not_active Expired
- 1970-11-09 ES ES385363A patent/ES385363A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016175668A1 (en) | 2015-04-28 | 2016-11-03 | Politechnika Rzeszowska | Preparation method for 1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione and 1-phenyl-2,6-bis(2-hydroxypropyl)imidazo[1,5-c]quinazoline-3,5-dione |
Also Published As
| Publication number | Publication date |
|---|---|
| YU34126B (en) | 1978-12-31 |
| BR6914069D0 (pt) | 1973-04-05 |
| YU245070A (en) | 1978-06-30 |
| ES385362A1 (es) | 1973-11-16 |
| JPS5034031B1 (enrdf_load_stackoverflow) | 1975-11-05 |
| JPS5034032B1 (enrdf_load_stackoverflow) | 1975-11-05 |
| CH525894A (de) | 1972-07-31 |
| SE359544B (enrdf_load_stackoverflow) | 1973-09-03 |
| CS160115B2 (enrdf_load_stackoverflow) | 1975-02-28 |
| CS160116B2 (enrdf_load_stackoverflow) | 1975-02-28 |
| ES385363A1 (es) | 1973-11-16 |
| SU398028A3 (enrdf_load_stackoverflow) | 1973-09-17 |
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