DE2135644A1 - Verfahren zur herstellung cyclischer imidsaeureester - Google Patents
Verfahren zur herstellung cyclischer imidsaeureesterInfo
- Publication number
- DE2135644A1 DE2135644A1 DE19712135644 DE2135644A DE2135644A1 DE 2135644 A1 DE2135644 A1 DE 2135644A1 DE 19712135644 DE19712135644 DE 19712135644 DE 2135644 A DE2135644 A DE 2135644A DE 2135644 A1 DE2135644 A1 DE 2135644A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- mol
- oxazoline
- bis
- dihydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 cyclic imide Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 title description 2
- 150000002148 esters Chemical class 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 9
- 125000002560 nitrile group Chemical group 0.000 claims description 8
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- LUSYNJGQFRRKIA-UHFFFAOYSA-N 5,6-dihydro-2h-1,3-oxazine Chemical compound C1CC=NCO1 LUSYNJGQFRRKIA-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 150000002918 oxazolines Chemical class 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000004893 oxazines Chemical class 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 150000000376 2-oxazolines Chemical class 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- YFDJCWXBKWRDPW-UHFFFAOYSA-N 4-propan-2-ylbenzonitrile Chemical compound CC(C)C1=CC=C(C#N)C=C1 YFDJCWXBKWRDPW-UHFFFAOYSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241001057495 Neda Species 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712135644 DE2135644A1 (de) | 1971-07-16 | 1971-07-16 | Verfahren zur herstellung cyclischer imidsaeureester |
| CH1063472A CH585211A5 (OSRAM) | 1971-07-16 | 1972-07-14 | |
| GB3310972A GB1369129A (en) | 1971-07-16 | 1972-07-14 | Cyclic imidic acid esters and process for their production |
| NL7209762A NL7209762A (OSRAM) | 1971-07-16 | 1972-07-14 | |
| BE786321A BE786321A (fr) | 1971-07-16 | 1972-07-14 | Procede de preparation d'esters d'imidoacide cycliques, et produits obtenus |
| IT2698072A IT1034028B (it) | 1971-07-16 | 1972-07-14 | Procedimento per la produzione di estere ciclico di imidoaido |
| FR7225758A FR2146790A5 (OSRAM) | 1971-07-16 | 1972-07-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712135644 DE2135644A1 (de) | 1971-07-16 | 1971-07-16 | Verfahren zur herstellung cyclischer imidsaeureester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2135644A1 true DE2135644A1 (de) | 1973-02-01 |
Family
ID=5813928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712135644 Pending DE2135644A1 (de) | 1971-07-16 | 1971-07-16 | Verfahren zur herstellung cyclischer imidsaeureester |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE786321A (OSRAM) |
| CH (1) | CH585211A5 (OSRAM) |
| DE (1) | DE2135644A1 (OSRAM) |
| FR (1) | FR2146790A5 (OSRAM) |
| GB (1) | GB1369129A (OSRAM) |
| IT (1) | IT1034028B (OSRAM) |
| NL (1) | NL7209762A (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3224880A1 (de) * | 1982-07-03 | 1984-01-05 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von reinen, wasserfreien imidsaeureestern durch umsetzung von nitrilen mit aminoalkoholen |
| EP2166005A1 (de) | 2008-09-23 | 2010-03-24 | Evonik Degussa GmbH | Verfahren zur Herstellung von Phenylenbisoxazolinen |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010044050A1 (de) | 2010-11-17 | 2012-05-24 | Evonik Degussa Gmbh | Verfahren zur kontinuierlichen Herstellung eines Prepolymers basierend auf Phenolharzen, Oxazolinen und Epoxiden |
-
1971
- 1971-07-16 DE DE19712135644 patent/DE2135644A1/de active Pending
-
1972
- 1972-07-14 BE BE786321A patent/BE786321A/xx unknown
- 1972-07-14 CH CH1063472A patent/CH585211A5/xx not_active IP Right Cessation
- 1972-07-14 NL NL7209762A patent/NL7209762A/xx unknown
- 1972-07-14 GB GB3310972A patent/GB1369129A/en not_active Expired
- 1972-07-14 IT IT2698072A patent/IT1034028B/it active
- 1972-07-17 FR FR7225758A patent/FR2146790A5/fr not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3224880A1 (de) * | 1982-07-03 | 1984-01-05 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von reinen, wasserfreien imidsaeureestern durch umsetzung von nitrilen mit aminoalkoholen |
| EP0098356A3 (en) * | 1982-07-03 | 1985-01-23 | Chemische Werke Huls Ag | Process for the preparation of pure anhydrous imido-acid esters by the reaction between nitriles and amino-alcohols |
| EP2166005A1 (de) | 2008-09-23 | 2010-03-24 | Evonik Degussa GmbH | Verfahren zur Herstellung von Phenylenbisoxazolinen |
| WO2010034562A1 (de) * | 2008-09-23 | 2010-04-01 | Evonik Degussa Gmbh | Verfahren zur herstellung von phenylenbisoxazolinen |
| US8222406B2 (en) | 2008-09-23 | 2012-07-17 | Evonik Degussa Gmbh | Process for preparing heterocycles |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1369129A (en) | 1974-10-02 |
| CH585211A5 (OSRAM) | 1977-02-28 |
| BE786321A (fr) | 1972-11-03 |
| IT1034028B (it) | 1979-09-10 |
| NL7209762A (OSRAM) | 1973-01-18 |
| FR2146790A5 (OSRAM) | 1973-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |