SU489327A3 - Способ получени четырех замещенных имидазолинов - Google Patents
Способ получени четырех замещенных имидазолиновInfo
- Publication number
- SU489327A3 SU489327A3 SU1841352A SU1841352A SU489327A3 SU 489327 A3 SU489327 A3 SU 489327A3 SU 1841352 A SU1841352 A SU 1841352A SU 1841352 A SU1841352 A SU 1841352A SU 489327 A3 SU489327 A3 SU 489327A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- product
- methyl
- phenyl
- ethanol
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- 150000002462 imidazolines Chemical class 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 239000000047 product Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- HOZLOOPIXHWKCI-UHFFFAOYSA-N 2-chloro-n-methylacetamide Chemical compound CNC(=O)CCl HOZLOOPIXHWKCI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- -1 1- (I-chlorophenyl) -2methylamino-4-oxo-2-imidazoline Chemical compound 0.000 description 2
- DSCWHNKZIWFACR-UHFFFAOYSA-N 1-methylimidazolidin-4-one Chemical compound CN1CNC(=O)C1 DSCWHNKZIWFACR-UHFFFAOYSA-N 0.000 description 2
- YGOBAQVJSUDQFU-UHFFFAOYSA-N 2-amino-1-methyl-4h-imidazol-5-one Chemical compound CN1C(=O)CN=C1N YGOBAQVJSUDQFU-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- GWRBRKFJOOUBPB-UHFFFAOYSA-N CC(N)=O.NC1=CC=CC=C1 Chemical compound CC(N)=O.NC1=CC=CC=C1 GWRBRKFJOOUBPB-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical compound C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 description 1
- YJELUYAPPFUYLW-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidine-2,5-diimine Chemical compound N=C1OC(=N)CN1C1=CC=CC=C1 YJELUYAPPFUYLW-UHFFFAOYSA-N 0.000 description 1
- FPVAAVCVHRVPNQ-UHFFFAOYSA-N 5-amino-3-phenyl-4h-imidazol-2-one Chemical compound C1C(N)=NC(=O)N1C1=CC=CC=C1 FPVAAVCVHRVPNQ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring 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
- C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen atoms
-
- 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
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 |
|---|---|---|---|
| US19147071A | 1971-10-21 | 1971-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU489327A3 true SU489327A3 (ru) | 1975-10-25 |
Family
ID=22705628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1841352A SU489327A3 (ru) | 1971-10-21 | 1972-10-20 | Способ получени четырех замещенных имидазолинов |
Country Status (15)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2933917A1 (de) * | 1979-08-22 | 1981-03-26 | Basf Ag, 67063 Ludwigshafen | 5-imino-imidazolidin-2-one und diese enthaltende herbizide. |
| DE3342849A1 (de) * | 1983-11-26 | 1985-06-13 | Erwin Mehne GmbH & Co, 7100 Heilbronn | Containertransportsystem |
| DE19532668A1 (de) | 1995-09-05 | 1997-03-06 | Dresden Arzneimittel | Neue, antikonvulsiv wirkende 1-Ar(alk)yl-imidazolin-2-one, die in 4-Stellung einen disubstituierten Amin-Rest enthalten, und Verfahren zu deren Herstellung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE281051C (enrdf_load_stackoverflow) * | ||||
| US2557911A (en) * | 1950-04-19 | 1951-06-19 | American Cyanamid Co | Method of preparing glycocyamidines |
-
0
- BE BE790380D patent/BE790380A/xx unknown
-
1972
- 1972-10-10 GB GB4673572A patent/GB1367576A/en not_active Expired
- 1972-10-11 ZA ZA727251A patent/ZA727251B/xx unknown
- 1972-10-12 AU AU47712/72A patent/AU476564B2/en not_active Expired
- 1972-10-18 AR AR244682A patent/AR197582A1/es active
- 1972-10-19 DE DE2251354A patent/DE2251354A1/de active Pending
- 1972-10-19 FR FR7237113A patent/FR2161917B1/fr not_active Expired
- 1972-10-20 BG BG21685A patent/BG20185A1/xx unknown
- 1972-10-20 CH CH1539772A patent/CH577979A5/xx not_active IP Right Cessation
- 1972-10-20 NL NL7214244A patent/NL7214244A/xx unknown
- 1972-10-20 SU SU1841352A patent/SU489327A3/ru active
- 1972-10-21 ES ES407856A patent/ES407856A1/es not_active Expired
- 1972-10-21 JP JP47105764A patent/JPS4849909A/ja active Pending
- 1972-10-23 DD DD166414A patent/DD102695A5/xx unknown
- 1972-10-23 CA CA154,611A patent/CA1000714A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1000714A (en) | 1976-11-30 |
| FR2161917A1 (enrdf_load_stackoverflow) | 1973-07-13 |
| DD102695A5 (enrdf_load_stackoverflow) | 1973-12-20 |
| CH577979A5 (enrdf_load_stackoverflow) | 1976-07-30 |
| ZA727251B (en) | 1973-06-27 |
| GB1367576A (en) | 1974-09-18 |
| AU4771272A (en) | 1974-04-26 |
| DE2251354A1 (de) | 1973-04-26 |
| FR2161917B1 (enrdf_load_stackoverflow) | 1976-08-20 |
| AU476564B2 (en) | 1976-09-30 |
| JPS4849909A (enrdf_load_stackoverflow) | 1973-07-14 |
| ES407856A1 (es) | 1976-01-16 |
| BG20185A1 (enrdf_load_stackoverflow) | 1975-11-05 |
| BE790380A (fr) | 1973-04-20 |
| NL7214244A (enrdf_load_stackoverflow) | 1973-04-25 |
| AR197582A1 (es) | 1974-04-23 |
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