CH507255A - Verfahren zur Herstellung von 2-(Halogenphenylamino)-imidazolin-2-Derivaten - Google Patents
Verfahren zur Herstellung von 2-(Halogenphenylamino)-imidazolin-2-DerivatenInfo
- Publication number
- CH507255A CH507255A CH1672668A CH1672668A CH507255A CH 507255 A CH507255 A CH 507255A CH 1672668 A CH1672668 A CH 1672668A CH 1672668 A CH1672668 A CH 1672668A CH 507255 A CH507255 A CH 507255A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethylenediamine
- imidazoline
- substd
- derivatives
- monosalt
- Prior art date
Links
- 150000001912 cyanamides Chemical class 0.000 title description 4
- 150000002462 imidazolines Chemical class 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- HVCCFMAPGCBCHZ-UHFFFAOYSA-N 2-aminoethylazanium;4-methylbenzenesulfonate Chemical compound NCCN.CC1=CC=C(S(O)(=O)=O)C=C1 HVCCFMAPGCBCHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001298 alcohols Chemical class 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract description 4
- WRDIIXFFFMAOHI-UHFFFAOYSA-N (2,6-dichlorophenyl)cyanamide Chemical compound ClC1=CC=CC(Cl)=C1NC#N WRDIIXFFFMAOHI-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000047 product Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 150000003840 hydrochlorides Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PWZKESLISFPGHR-UHFFFAOYSA-N (2-chlorophenyl)cyanamide Chemical compound ClC1=CC=CC=C1NC#N PWZKESLISFPGHR-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- VVOHXEPTFUXUFX-UHFFFAOYSA-N (3,4-dichlorophenyl)methylcyanamide Chemical compound N#CNCC1=CC(=C(C=C1)Cl)Cl VVOHXEPTFUXUFX-UHFFFAOYSA-N 0.000 description 1
- -1 (dichlorobenzyl) -guanidines Chemical class 0.000 description 1
- MRXYVMXWTBRRSB-UHFFFAOYSA-N 2-[2-(diaminomethylideneamino)ethyl]guanidine Chemical compound NC(N)=NCCN=C(N)N MRXYVMXWTBRRSB-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical compound NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 1
- 101150070189 CIN3 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- LTALGLGRMHWWKA-UHFFFAOYSA-N ethane-1,2-diamine;hydroiodide Chemical compound [I-].NCC[NH3+] LTALGLGRMHWWKA-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical class NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- C07D233/28—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 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD13077768 | 1968-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH507255A true CH507255A (de) | 1971-05-15 |
Family
ID=5479812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1672668A CH507255A (de) | 1968-03-11 | 1968-11-08 | Verfahren zur Herstellung von 2-(Halogenphenylamino)-imidazolin-2-Derivaten |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT278000B (da) |
| BG (1) | BG19459A1 (da) |
| CH (1) | CH507255A (da) |
| DK (1) | DK117497B (da) |
| FI (1) | FI56173C (da) |
| PL (1) | PL71336B1 (da) |
| SE (1) | SE366745B (da) |
| YU (1) | YU31836B (da) |
-
1968
- 1968-07-19 AT AT06999/68A patent/AT278000B/de not_active IP Right Cessation
- 1968-08-13 YU YU192468A patent/YU31836B/xx unknown
- 1968-08-14 FI FI229468A patent/FI56173C/fi active
- 1968-08-17 BG BG1051368A patent/BG19459A1/xx unknown
- 1968-08-27 DK DK411468A patent/DK117497B/da unknown
- 1968-09-23 SE SE1280868A patent/SE366745B/xx unknown
- 1968-11-08 CH CH1672668A patent/CH507255A/de not_active IP Right Cessation
-
1969
- 1969-02-24 PL PL13192169A patent/PL71336B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU192468A (en) | 1973-06-30 |
| FI56173C (fi) | 1979-12-10 |
| FI56173B (fi) | 1979-08-31 |
| SE366745B (da) | 1974-05-06 |
| BG19459A1 (da) | 1975-06-25 |
| AT278000B (de) | 1970-01-12 |
| PL71336B1 (da) | 1974-06-29 |
| DK117497B (da) | 1970-05-04 |
| YU31836B (en) | 1973-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH409980A (de) | Verfahren zur Herstellung von substituierten 2-Arylamino-1,3-diazacycloalkenen | |
| DE1445743A1 (de) | Verfahren zur Herstellung von in 2-Stellung substituierten Benzoxazinonen | |
| DE2505297C3 (de) | Verfahren zur Herstellung von in 2- und 6-Stellung des Phenylkerns substituierten 2-Phenylamino-2-imidazoun-Derivaten | |
| DE2429937C2 (da) | ||
| DE2316377B2 (de) | Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen | |
| CH646156A5 (de) | Schwefelhaltige benzimidazol-derivate und verfahren zu ihrer herstellung. | |
| DE1176660B (de) | Verfahren zur Herstellung von triaryl-substituierten Imidazolinonen-4(5) | |
| DE941288C (de) | Verfahren zur Herstellung substituierter 2-Imino-4-thiazoline oder von Salzen derselben bzw. von substituierten 2-Aminothiazolen | |
| EP0179408A2 (de) | Neue Amidoalkylmelamine und Aminoalkylmelamine und Verfahren zu ihrer Herstellung | |
| DE2124907A1 (de) | 3 Amino 1,2,4 oxadiazole, Verfahren zu ihrer Herstellung und Arzneipraparate | |
| CH507255A (de) | Verfahren zur Herstellung von 2-(Halogenphenylamino)-imidazolin-2-Derivaten | |
| DE2429746C3 (de) | Verfahren zur Herstellung von Triacetonamin | |
| DE60202245T2 (de) | Herstellungsmethode von Famciclovir und Herstellungs- bzw. Kristallisationsmethode eines entsprechenden Intermediates | |
| DE1770874B2 (de) | Verfahren zur herstellung von 2-(2,6- dichlorphenylamino)-imidazolin-2 | |
| CH495360A (de) | Verfahren zur Herstellung von 2-Carbalkoxyamino-benzimidazolen | |
| DE2640616C3 (de) | Verfahren zur Herstellung von N-Acyl-2-aiylglycinen | |
| DE2438077A1 (de) | Verfahren zur herstellung von propanolaminderivaten und nach dem verfahren hergestellte propanolaminderivate | |
| CH642617A5 (de) | Verfahren zur herstellung von bromhexin. | |
| DE737931C (de) | Verfahren zur Herstellung von 2, 4-Diaminochinazolin | |
| DE2742158B2 (de) | Verfahren zur Herstellung substituierter Harnstoffe | |
| DE2104682C3 (de) | Verfahren zur Herstellung von o-Sulfamidobenzoesäuren | |
| AT372940B (de) | Verfahren zur herstellung von (d)-(-)-phydroxyphenylglycylchlorid-hydrochlorid | |
| DE1670675A1 (de) | Verfahren zur Herstellung von 2-Arylamino-4,6-dichlor-s-Triazinen | |
| AT218534B (de) | Verfahren zur Herstellung von neuen substituierten Harnstoffen | |
| AT214440B (de) | Verfahren zur Herstellung von 3-Iminoisoindolin-1-onen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |