DE3102359A1 - Verfahren zur herstellung von oxazolidin-2,4-dionen - Google Patents
Verfahren zur herstellung von oxazolidin-2,4-dionenInfo
- Publication number
- DE3102359A1 DE3102359A1 DE3102359A DE3102359A DE3102359A1 DE 3102359 A1 DE3102359 A1 DE 3102359A1 DE 3102359 A DE3102359 A DE 3102359A DE 3102359 A DE3102359 A DE 3102359A DE 3102359 A1 DE3102359 A1 DE 3102359A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- halogen
- dichlorophenyl
- radical
- oxazolidine
- 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.)
- Withdrawn
Links
- 150000001477 2,4-oxazolidinediones Chemical class 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 150000001408 amides Chemical class 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract description 5
- 150000002989 phenols Chemical class 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 150000004651 carbonic acid esters Chemical class 0.000 claims abstract description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 3
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- -1 methoxy Aryl radical Chemical class 0.000 claims description 17
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims description 3
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 238000004821 distillation Methods 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- 125000001624 naphthyl group Chemical group 0.000 abstract description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 4
- FBYYIBNYONAZCU-UHFFFAOYSA-N M2 Chemical compound C=CC(O)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 FBYYIBNYONAZCU-UHFFFAOYSA-N 0.000 description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ADQLPWFWLUKIFM-UHFFFAOYSA-N ClC=1C=C(C=C(C1)Cl)N1COC(C1)(C)C=C Chemical compound ClC=1C=C(C=C(C1)Cl)N1COC(C1)(C)C=C ADQLPWFWLUKIFM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZQSJHAVRVHMPCE-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-hydroxy-3-methoxy-2-methylpropanamide Chemical compound COCC(C)(O)C(=O)NC1=CC(Cl)=CC(Cl)=C1 ZQSJHAVRVHMPCE-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- C07D263/30—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
- C07D263/44—Two oxygen atoms
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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3102359A DE3102359A1 (de) | 1981-01-24 | 1981-01-24 | Verfahren zur herstellung von oxazolidin-2,4-dionen |
| GR66823A GR77325B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-01-24 | 1981-12-17 | |
| EP82100306A EP0056966B1 (de) | 1981-01-24 | 1982-01-18 | Verfahren zur Herstellung von Oxazolidin-2,4-dionen |
| DE8282100306T DE3260914D1 (en) | 1981-01-24 | 1982-01-18 | Process for the preparation of 2,4-oxazolidine diones |
| AT82100306T ATE9801T1 (de) | 1981-01-24 | 1982-01-18 | Verfahren zur herstellung von oxazolidin-2,4dionen. |
| DK027382A DK150140C (da) | 1981-01-24 | 1982-01-22 | Fremgangsmaade til fremstilling af oxazolidin-2,4-dioner |
| IE138/82A IE52262B1 (en) | 1981-01-24 | 1982-01-22 | Preparation of oxazolidine-2,4-diones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3102359A DE3102359A1 (de) | 1981-01-24 | 1981-01-24 | Verfahren zur herstellung von oxazolidin-2,4-dionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3102359A1 true DE3102359A1 (de) | 1982-08-19 |
Family
ID=6123295
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3102359A Withdrawn DE3102359A1 (de) | 1981-01-24 | 1981-01-24 | Verfahren zur herstellung von oxazolidin-2,4-dionen |
| DE8282100306T Expired DE3260914D1 (en) | 1981-01-24 | 1982-01-18 | Process for the preparation of 2,4-oxazolidine diones |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282100306T Expired DE3260914D1 (en) | 1981-01-24 | 1982-01-18 | Process for the preparation of 2,4-oxazolidine diones |
Country Status (6)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19613333A1 (de) * | 1996-04-03 | 1997-10-09 | Bayer Ag | Verfahren zur Herstellung von Oxazolidin-2,4-dionen |
| CN103974691A (zh) * | 2011-12-15 | 2014-08-06 | 高露洁-棕榄公司 | 水性口腔护理组合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2338220A (en) * | 1942-01-31 | 1944-01-04 | Mallinckrodt Chemical Works | Process of making oxazolidinediones |
| US2909467A (en) * | 1958-07-09 | 1959-10-20 | Us Vitamin Pharm Corp | 3-(d-alpha-methylphenethyl)-5-methyl-1, 3-oxazolidine-2, 4-dione |
| US2928840A (en) * | 1958-11-26 | 1960-03-15 | Us Vitamin Pharm Corp | 3-(o-substituted phenyl) oxazolidinediones and process therefor |
| DE1813434A1 (de) * | 1968-12-07 | 1970-06-25 | Bayer Ag | Verfahren zur Herstellung von omikron-Hydroxy-aralkylaethern |
| DE2527677A1 (de) * | 1975-06-21 | 1977-01-20 | Bayer Ag | Verfahren zur herstellung von 2,4- dioxo-1,2,3,4-tetrahydro-s-triazino- eckige klammer auf 1,2-a eckige klammer zu -benzimidazolen |
| DE2813873A1 (de) * | 1978-03-31 | 1979-10-11 | Basf Ag | Verfahren zur herstellung von oxazolidin-2,4-dionen |
| DE2827414A1 (de) * | 1978-06-22 | 1980-01-10 | Basf Ag | Verfahren zur herstellung von oxazolidin-2,4-dionen |
-
1981
- 1981-01-24 DE DE3102359A patent/DE3102359A1/de not_active Withdrawn
- 1981-12-17 GR GR66823A patent/GR77325B/el unknown
-
1982
- 1982-01-18 DE DE8282100306T patent/DE3260914D1/de not_active Expired
- 1982-01-18 AT AT82100306T patent/ATE9801T1/de not_active IP Right Cessation
- 1982-01-18 EP EP82100306A patent/EP0056966B1/de not_active Expired
- 1982-01-22 IE IE138/82A patent/IE52262B1/en unknown
- 1982-01-22 DK DK027382A patent/DK150140C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0056966B1 (de) | 1984-10-10 |
| IE52262B1 (en) | 1987-08-19 |
| DK150140C (da) | 1987-06-15 |
| DK27382A (da) | 1982-07-25 |
| DE3260914D1 (en) | 1984-11-15 |
| EP0056966A1 (de) | 1982-08-04 |
| IE820138L (en) | 1982-07-24 |
| DK150140B (da) | 1986-12-15 |
| GR77325B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-09-11 |
| ATE9801T1 (de) | 1984-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |