NO123850B - - Google Patents
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- Publication number
- NO123850B NO123850B NO2004/68A NO200468A NO123850B NO 123850 B NO123850 B NO 123850B NO 2004/68 A NO2004/68 A NO 2004/68A NO 200468 A NO200468 A NO 200468A NO 123850 B NO123850 B NO 123850B
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- naphthyl
- imidazoline
- methyl
- acetonitrile
- Prior art date
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 241000700198 Cavia Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal cyanide Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical compound [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH741567A CH469007A (fr) | 1967-05-25 | 1967-05-25 | Procédé de préparation d'un nouveau dérivé de l'imidazoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123850B true NO123850B (en:Method) | 1972-01-24 |
Family
ID=4324768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2004/68A NO123850B (en:Method) | 1967-05-25 | 1968-05-22 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3546242A (en:Method) |
| AT (1) | AT277237B (en:Method) |
| BE (1) | BE713057A (en:Method) |
| CH (1) | CH469007A (en:Method) |
| DK (1) | DK117901B (en:Method) |
| ES (1) | ES352647A1 (en:Method) |
| FR (2) | FR1566851A (en:Method) |
| GB (1) | GB1158250A (en:Method) |
| IL (1) | IL29800A (en:Method) |
| NL (1) | NL6806813A (en:Method) |
| NO (1) | NO123850B (en:Method) |
| SE (1) | SE337826B (en:Method) |
| YU (1) | YU117868A (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1266897A3 (en) * | 1997-12-19 | 2003-12-03 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| EP0924209B1 (en) * | 1997-12-19 | 2003-05-02 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| GB2351082A (en) * | 1999-06-18 | 2000-12-20 | Lilly Forschung Gmbh | Synthesis of Cyclic Substituted Amidines |
| US20040009976A1 (en) * | 2002-04-30 | 2004-01-15 | Kumiko Takeuchi | Hypoglycemic imidazoline compounds |
| CN103224468A (zh) * | 2013-05-10 | 2013-07-31 | 范强 | 四氢唑林的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2948724A (en) * | 1958-04-21 | 1960-08-09 | Sahyun | Halogenated derivatives of tetrahydro-1-naphthyl cyclic amidines |
-
1967
- 1967-05-25 CH CH741567A patent/CH469007A/fr unknown
-
1968
- 1968-04-01 BE BE713057D patent/BE713057A/xx unknown
- 1968-04-10 IL IL29800A patent/IL29800A/xx unknown
- 1968-04-10 ES ES352647A patent/ES352647A1/es not_active Expired
- 1968-04-19 AT AT384668A patent/AT277237B/de not_active IP Right Cessation
- 1968-04-22 FR FR1566851D patent/FR1566851A/fr not_active Expired
- 1968-05-09 DK DK220568AA patent/DK117901B/da unknown
- 1968-05-10 US US728342A patent/US3546242A/en not_active Expired - Lifetime
- 1968-05-13 GB GB22585/68A patent/GB1158250A/en not_active Expired
- 1968-05-14 NL NL6806813A patent/NL6806813A/xx unknown
- 1968-05-20 YU YU01178/68A patent/YU117868A/xx unknown
- 1968-05-22 NO NO2004/68A patent/NO123850B/no unknown
- 1968-05-22 SE SE06949/68A patent/SE337826B/xx unknown
- 1968-07-16 FR FR159357A patent/FR7670M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| YU117868A (en) | 1973-10-31 |
| IL29800A0 (en) | 1968-06-20 |
| GB1158250A (en) | 1969-07-16 |
| NL6806813A (en:Method) | 1968-11-26 |
| AT277237B (de) | 1969-12-10 |
| DE1770476A1 (en:Method) | 1972-07-06 |
| IL29800A (en) | 1971-04-28 |
| US3546242A (en) | 1970-12-08 |
| ES352647A1 (es) | 1969-08-16 |
| FR1566851A (en:Method) | 1969-05-09 |
| FR7670M (en:Method) | 1970-02-09 |
| DK117901B (da) | 1970-06-15 |
| SE337826B (en:Method) | 1971-08-23 |
| BE713057A (en:Method) | 1968-08-16 |
| CH469007A (fr) | 1969-02-28 |
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