DE1670557A1 - Verfahren zur Herstellung von 2-substituierten N-Acyloxazolidinen - Google Patents
Verfahren zur Herstellung von 2-substituierten N-AcyloxazolidinenInfo
- Publication number
- DE1670557A1 DE1670557A1 DE19671670557 DE1670557A DE1670557A1 DE 1670557 A1 DE1670557 A1 DE 1670557A1 DE 19671670557 DE19671670557 DE 19671670557 DE 1670557 A DE1670557 A DE 1670557A DE 1670557 A1 DE1670557 A1 DE 1670557A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxyethyl
- amides
- mol
- aldehydes
- acyloxazolidines
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000002917 oxazolidines Chemical class 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 230000002779 inactivation Effects 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- -1 2-hydroxyethylyl Chemical group 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- LMVSBYPDMNAXPF-UHFFFAOYSA-N N-(decanoyl)ethanolamine Chemical compound CCCCCCCCCC(=O)NCCO LMVSBYPDMNAXPF-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- RESUUYRNXHKOOT-UHFFFAOYSA-N 1-(2-phenyl-1,3-oxazolidin-3-yl)propan-1-one Chemical compound C1(=CC=CC=C1)C1OCCN1C(CC)=O RESUUYRNXHKOOT-UHFFFAOYSA-N 0.000 description 1
- GCTSOJFGLXHUMW-UHFFFAOYSA-N 1-(2-propyl-1,3-oxazolidin-3-yl)hexan-1-one Chemical compound C(CC)C1OCCN1C(CCCCC)=O GCTSOJFGLXHUMW-UHFFFAOYSA-N 0.000 description 1
- ZJLIJZUCZSGYBM-UHFFFAOYSA-N 2-propyl-1,3-oxazolidine Chemical class CCCC1NCCO1 ZJLIJZUCZSGYBM-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- AYSMJZQOJHKFQC-UHFFFAOYSA-N C(C)(C)C1OCCN1C(CCCCCC)=O Chemical compound C(C)(C)C1OCCN1C(CCCCCC)=O AYSMJZQOJHKFQC-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GSILMNFJLONLCJ-UHFFFAOYSA-N N-(octanoyl)ethanolamine Chemical compound CCCCCCCC(=O)NCCO GSILMNFJLONLCJ-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000010626 work up procedure 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
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/06—Seven-membered rings having the hetero atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0052590 | 1967-03-21 | ||
| DED0052935 | 1967-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670557A1 true DE1670557A1 (de) | 1971-07-01 |
Family
ID=25972572
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671670557 Pending DE1670557A1 (de) | 1967-03-21 | 1967-03-21 | Verfahren zur Herstellung von 2-substituierten N-Acyloxazolidinen |
| DE19671593824 Pending DE1593824A1 (de) | 1967-03-21 | 1967-04-27 | Verfahren zur Herstellung von Carbonsaeure-2-aryloxyaethylestern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671593824 Pending DE1593824A1 (de) | 1967-03-21 | 1967-04-27 | Verfahren zur Herstellung von Carbonsaeure-2-aryloxyaethylestern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3557167A (enExample) |
| BE (2) | BE712499A (enExample) |
| CH (1) | CH494205A (enExample) |
| DE (2) | DE1670557A1 (enExample) |
| FR (2) | FR95494E (enExample) |
| GB (2) | GB1150620A (enExample) |
| LU (1) | LU55760A1 (enExample) |
| NL (1) | NL6803999A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204705A1 (es) * | 1972-10-13 | 1976-02-27 | Stauffer Chemical Co | Nuevo compuesto antidoto derivado de 3-acil oxazolidinas y tiazolidinas sustituidas util para composiciones herbicidas y la composicion herbicida que lo contiene |
| CA1014563A (en) * | 1972-10-13 | 1977-07-26 | Stauffer Chemical Company | Substituted oxazolidines and thiazolidines |
| EP0002329A1 (en) * | 1977-11-30 | 1979-06-13 | Imperial Chemical Industries Plc | Plasticized polyvinylchloride compositions |
| US4478754A (en) * | 1982-11-01 | 1984-10-23 | The Procter & Gamble Company | Preparation of phenyl esters in the presence of boric anhydride |
| DE3814781A1 (de) * | 1988-04-30 | 1989-11-09 | Basf Ag | Verfahren zur herstellung von 2-hydroxy-4-(2'-hydroxyethoxy)-benzophenonen |
| US5560872A (en) * | 1995-05-18 | 1996-10-01 | Lever Brothers Company | Compositions comprising oxazolidine and tetrahydrooxazine amide surfactants |
| GB0408288D0 (en) * | 2004-04-14 | 2004-05-19 | Unilever Plc | Antiperspirant compositions |
| US10899698B2 (en) * | 2010-10-26 | 2021-01-26 | Ethox Chemicals, Llc | Bis(aryloxyalkyl) esters of aromatic polycarboxylic acids and method of preparation |
| US8344172B2 (en) | 2011-03-25 | 2013-01-01 | Stepan Company | Preparation of antiplasticizers for thermoplastic polyesters |
-
1967
- 1967-03-21 DE DE19671670557 patent/DE1670557A1/de active Pending
- 1967-04-27 DE DE19671593824 patent/DE1593824A1/de active Pending
-
1968
- 1968-03-20 BE BE712499D patent/BE712499A/xx unknown
- 1968-03-21 GB GB13768/68A patent/GB1150620A/en not_active Expired
- 1968-03-21 NL NL6803999A patent/NL6803999A/xx unknown
- 1968-03-21 FR FR144825A patent/FR95494E/fr not_active Expired
- 1968-03-25 LU LU55760D patent/LU55760A1/xx unknown
- 1968-03-28 CH CH460068A patent/CH494205A/de not_active IP Right Cessation
- 1968-04-16 BE BE713738D patent/BE713738A/xx unknown
- 1968-04-24 FR FR149260A patent/FR1560184A/fr not_active Expired
- 1968-04-26 US US724630A patent/US3557167A/en not_active Expired - Lifetime
- 1968-04-26 GB GB20013/68A patent/GB1182081A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR95494E (fr) | 1971-01-15 |
| BE712499A (enExample) | 1968-09-28 |
| GB1150620A (en) | 1969-04-30 |
| DE1593824A1 (de) | 1970-12-10 |
| US3557167A (en) | 1971-01-19 |
| GB1182081A (en) | 1970-02-25 |
| NL6803999A (enExample) | 1968-09-23 |
| CH494205A (de) | 1970-07-31 |
| FR1560184A (enExample) | 1969-02-03 |
| LU55760A1 (enExample) | 1968-03-25 |
| BE713738A (enExample) | 1968-10-16 |
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