CH666025A5 - 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkylester sowie deren herstellung. - Google Patents
4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkylester sowie deren herstellung. Download PDFInfo
- Publication number
- CH666025A5 CH666025A5 CH411985A CH411985A CH666025A5 CH 666025 A5 CH666025 A5 CH 666025A5 CH 411985 A CH411985 A CH 411985A CH 411985 A CH411985 A CH 411985A CH 666025 A5 CH666025 A5 CH 666025A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrrolin
- alkoxy
- acid
- alkyl
- alkyl ester
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- TXKQBYYDTLOLHA-UHFFFAOYSA-N 3-methoxy-1,2-dihydropyrrol-5-one Chemical compound COC1=CC(=O)NC1 TXKQBYYDTLOLHA-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 150000004678 hydrides Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- HFLMYYLFSNEOOT-UHFFFAOYSA-N methyl 4-chloro-3-oxobutanoate Chemical compound COC(=O)CC(=O)CCl HFLMYYLFSNEOOT-UHFFFAOYSA-N 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 4
- JNYMRXDQVPIONI-HWKANZROSA-N methyl (e)-4-chloro-3-methoxybut-2-enoate Chemical compound COC(=O)\C=C(/CCl)OC JNYMRXDQVPIONI-HWKANZROSA-N 0.000 claims description 4
- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000010626 work up procedure Methods 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- MVKLHAOLEIYVRH-UHFFFAOYSA-N C(C)(=O)OCCN1C(C=C(C1)OC)=O Chemical compound C(C)(=O)OCCN1C(C=C(C1)OC)=O MVKLHAOLEIYVRH-UHFFFAOYSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000001311 chemical methods and process Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- LJSRSOQMKIBVRH-UHFFFAOYSA-N ethyl 2-(3-methoxy-5-oxo-2h-pyrrol-1-yl)acetate Chemical compound CCOC(=O)CN1CC(OC)=CC1=O LJSRSOQMKIBVRH-UHFFFAOYSA-N 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- SIWVGXQOXWGJCI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;2-ethenylbenzenesulfonic acid Chemical compound C=CC1=CC=CC=C1C=C.OS(=O)(=O)C1=CC=CC=C1C=C SIWVGXQOXWGJCI-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 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
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CFGIKWDUNLXSIV-UHFFFAOYSA-N methyl 2-(3-methoxy-5-oxo-2h-pyrrol-1-yl)acetate Chemical compound COC(=O)CN1CC(OC)=CC1=O CFGIKWDUNLXSIV-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D207/30—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
- C07D207/38—2-Pyrrolones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH411985A CH666025A5 (de) | 1985-09-24 | 1985-09-24 | 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkylester sowie deren herstellung. |
| HU863310A HU195773B (en) | 1985-09-24 | 1986-08-01 | Process for preparing alkyl esters of 4-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid |
| IE216186A IE59030B1 (en) | 1985-09-24 | 1986-08-11 | 4-alkoxy-3-pyrrolin-2-on-1-ylacetic acid alkyl esters and process for the preparation thereof |
| CS600986A CS274660B2 (en) | 1985-09-24 | 1986-08-14 | Method of 4-alkoxy-3-pyrroline-2-on-1-yl-acetic acid's alkyl esters production |
| IL8679947A IL79947A (en) | 1985-09-24 | 1986-09-04 | 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid esters and process for their preparation |
| SU864028089A SU1468412A3 (ru) | 1985-09-24 | 1986-09-05 | Способ получени алкиловых эфиров 4-алкокси-3-пирролин-2-он-1-ил-уксусной кислоты |
| EP86112951A EP0216324B1 (de) | 1985-09-24 | 1986-09-19 | 4-Alkoxy-3-pyrrolin-2-on-1-yl-essigsäurealkyl- bzw. -benzylester sowie deren Herstellung |
| DE8686112951T DE3675722D1 (de) | 1985-09-24 | 1986-09-19 | 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkyl- bzw. -benzylester sowie deren herstellung. |
| JP61221770A JPH0742269B2 (ja) | 1985-09-24 | 1986-09-19 | ４−アルコキシ−３−ピロリン−２−オン−１−イル−酢酸アルキルエステルおよびその製造方法 |
| AT86112951T ATE58527T1 (de) | 1985-09-24 | 1986-09-19 | 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkylbzw. -benzylester sowie deren herstellung. |
| ES8602068A ES2001695A6 (es) | 1985-09-24 | 1986-09-22 | Procedimiento para preparar esteres alquilicos de c1-c4 de acido 4-alcoxi-3-pirrolin-2-on-1-il-acetico |
| DK453486A DK453486A (da) | 1985-09-24 | 1986-09-23 | 4-alkoxy-3-pyrrolin-2-on-1-yl-eddikesyre-alkylestere samt deres fremstilling |
| NO86863791A NO171848C (no) | 1985-09-24 | 1986-09-23 | Fremstilling av 4-alkoksy-3-pyrrolin-2-on-1-yl-eddiksyrealkylestere |
| CA000519007A CA1271769A (en) | 1985-09-24 | 1986-09-24 | 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters and their production |
| US06/931,849 US4780545A (en) | 1985-09-24 | 1986-11-18 | Production of 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters |
| US07/147,275 US4880940A (en) | 1985-09-24 | 1988-07-22 | 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH411985A CH666025A5 (de) | 1985-09-24 | 1985-09-24 | 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkylester sowie deren herstellung. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH666025A5 true CH666025A5 (de) | 1988-06-30 |
Family
ID=4270166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH411985A CH666025A5 (de) | 1985-09-24 | 1985-09-24 | 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkylester sowie deren herstellung. |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH666025A5 (cs) |
| CS (1) | CS274660B2 (cs) |
| SU (1) | SU1468412A3 (cs) |
-
1985
- 1985-09-24 CH CH411985A patent/CH666025A5/de not_active IP Right Cessation
-
1986
- 1986-08-14 CS CS600986A patent/CS274660B2/cs unknown
- 1986-09-05 SU SU864028089A patent/SU1468412A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CS274660B2 (en) | 1991-09-15 |
| CS600986A2 (en) | 1990-11-14 |
| SU1468412A3 (ru) | 1989-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |