SU893131A3 - Способ получени 2-оксопирролидин-N-алкиламидов - Google Patents
Способ получени 2-оксопирролидин-N-алкиламидов Download PDFInfo
- Publication number
- SU893131A3 SU893131A3 SU772439826A SU2439826A SU893131A3 SU 893131 A3 SU893131 A3 SU 893131A3 SU 772439826 A SU772439826 A SU 772439826A SU 2439826 A SU2439826 A SU 2439826A SU 893131 A3 SU893131 A3 SU 893131A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkylamides
- sodium
- oxopyrrolidine
- product
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000009833 condensation Methods 0.000 claims abstract description 4
- 230000005494 condensation Effects 0.000 claims abstract description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 5
- 229960002317 succinimide Drugs 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- RFIZPYFNEYSHKG-UHFFFAOYSA-N pyrrolidine-2,5-dione;sodium Chemical compound [Na].O=C1CCC(=O)N1 RFIZPYFNEYSHKG-UHFFFAOYSA-N 0.000 abstract description 7
- 230000009467 reduction Effects 0.000 abstract description 4
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 229940080818 propionamide Drugs 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005868 electrolysis reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- QAZCPUUJMFBNJO-UHFFFAOYSA-N pyrrolidin-2-one;sodium Chemical compound [Na].O=C1CCCN1 QAZCPUUJMFBNJO-UHFFFAOYSA-N 0.000 description 2
- QEWFNTGJRKCBES-UHFFFAOYSA-N pyrrolidine;sodium Chemical compound [Na].C1CCNC1 QEWFNTGJRKCBES-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- C07D207/34—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 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU78/76A YU39341B (en) | 1976-01-14 | 1976-01-14 | Process for obtaining n-alkylamide-2-oxopyrrolidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU893131A3 true SU893131A3 (ru) | 1981-12-23 |
Family
ID=25548234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772439826A SU893131A3 (ru) | 1976-01-14 | 1977-01-12 | Способ получени 2-оксопирролидин-N-алкиламидов |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS52116463A (enExample) |
| AT (1) | AT355013B (enExample) |
| CH (1) | CH624671A5 (enExample) |
| CS (1) | CS208719B2 (enExample) |
| FI (1) | FI63750C (enExample) |
| HU (1) | HU172999B (enExample) |
| PL (1) | PL103074B1 (enExample) |
| SE (1) | SE416730B (enExample) |
| SU (1) | SU893131A3 (enExample) |
| YU (1) | YU39341B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2629117C1 (ru) * | 2016-06-14 | 2017-08-24 | Сизов Владимир Владимирович | Способ получения 4-замещенного 2-[2-оксо-1-пирролидинил] ацетамида |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5933068A (ja) * | 1982-08-17 | 1984-02-22 | Nitsukuu Kogyo Kk | 真空含浸法 |
| JPS59152030A (ja) * | 1983-02-15 | 1984-08-30 | Taiho Kogyo Co Ltd | ダイカスト部品への含浸方法及び装置 |
| JPS59150655A (ja) * | 1983-04-14 | 1984-08-28 | Taiho Kogyo Co Ltd | ダイカスト部品への含浸方法及び装置 |
| JPS62218028A (ja) * | 1986-03-20 | 1987-09-25 | Toyota Motor Corp | 含浸処理方法 |
-
1976
- 1976-01-14 YU YU78/76A patent/YU39341B/xx unknown
- 1976-12-29 CH CH1643376A patent/CH624671A5/de not_active IP Right Cessation
- 1976-12-30 AT AT980876A patent/AT355013B/de not_active IP Right Cessation
-
1977
- 1977-01-04 CS CS7761A patent/CS208719B2/cs unknown
- 1977-01-10 SE SE7700172A patent/SE416730B/xx not_active IP Right Cessation
- 1977-01-11 HU HU77PI00000559A patent/HU172999B/hu unknown
- 1977-01-12 SU SU772439826A patent/SU893131A3/ru active
- 1977-01-12 PL PL1977195267A patent/PL103074B1/pl unknown
- 1977-01-12 FI FI770088A patent/FI63750C/fi not_active IP Right Cessation
- 1977-01-14 JP JP255077A patent/JPS52116463A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2629117C1 (ru) * | 2016-06-14 | 2017-08-24 | Сизов Владимир Владимирович | Способ получения 4-замещенного 2-[2-оксо-1-пирролидинил] ацетамида |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA980876A (de) | 1979-07-15 |
| HU172999B (hu) | 1979-01-28 |
| PL195267A1 (pl) | 1978-03-13 |
| CS208719B2 (en) | 1981-09-15 |
| JPS52116463A (en) | 1977-09-29 |
| AT355013B (de) | 1980-02-11 |
| JPS5744667B2 (enExample) | 1982-09-22 |
| FI63750C (fi) | 1983-08-10 |
| CH624671A5 (en) | 1981-08-14 |
| PL103074B1 (pl) | 1979-05-31 |
| YU7876A (en) | 1982-02-28 |
| FI63750B (fi) | 1983-04-29 |
| FI770088A7 (enExample) | 1977-07-15 |
| SE7700172L (sv) | 1977-07-15 |
| YU39341B (en) | 1984-10-31 |
| SE416730B (sv) | 1981-02-02 |
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