DE1216879B - Verfahren zur Herstellung von optisch aktiven Hydantoinderivaten - Google Patents
Verfahren zur Herstellung von optisch aktiven HydantoinderivatenInfo
- Publication number
- DE1216879B DE1216879B DEF41917A DEF0041917A DE1216879B DE 1216879 B DE1216879 B DE 1216879B DE F41917 A DEF41917 A DE F41917A DE F0041917 A DEF0041917 A DE F0041917A DE 1216879 B DE1216879 B DE 1216879B
- Authority
- DE
- Germany
- Prior art keywords
- optically active
- methylhydantoin
- crystals
- hydantoin derivatives
- alkyl
- 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 5
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title claims description 4
- 150000001469 hydantoins Chemical class 0.000 title claims description 4
- 239000000126 substance Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000012552 review Methods 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- -1 aralkyl radicals Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEBCWEDRGPSHQH-YUMQZZPRSA-N dipropan-2-yl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound CC(C)OC(=O)[C@@H](O)[C@H](O)C(=O)OC(C)C XEBCWEDRGPSHQH-YUMQZZPRSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- NKUJXLLJYFGACA-UHFFFAOYSA-N 2,3-dihydroxy-2,3-di(propan-2-yl)butanedioic acid Chemical class CC(C)C(O)(C(O)=O)C(O)(C(C)C)C(O)=O NKUJXLLJYFGACA-UHFFFAOYSA-N 0.000 description 1
- VMAQYKGITHDWKL-UHFFFAOYSA-N 5-Methyl hydantoin Natural products CC1NC(=O)NC1=O VMAQYKGITHDWKL-UHFFFAOYSA-N 0.000 description 1
- LMCMSORQDRGJLG-UHFFFAOYSA-N 5-[(3,4-dimethoxyphenyl)methyl]-5-methylimidazolidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC=C1CC1(C)C(=O)NC(=O)N1 LMCMSORQDRGJLG-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41917A DE1216879B (de) | 1964-02-05 | 1964-02-05 | Verfahren zur Herstellung von optisch aktiven Hydantoinderivaten |
| CH146465A CH439305A (de) | 1964-02-05 | 1965-02-03 | Verfahren zur Herstellung optisch aktiver Hydantoinderivate |
| AT98265A AT250986B (de) | 1964-02-05 | 1965-02-04 | Verfahren zur Herstellung von optisch aktiven Hydantoinderivaten |
| NL6501504A NL6501504A (enrdf_load_stackoverflow) | 1964-02-05 | 1965-02-05 | |
| GB516665A GB1039969A (en) | 1964-02-05 | 1965-02-05 | Process for the production of optically-active hydantoin derivatives |
| BE659315D BE659315A (enrdf_load_stackoverflow) | 1964-02-05 | 1965-02-05 | |
| FR4611A FR1425595A (fr) | 1964-02-05 | 1965-02-05 | Procédé de fabrication de dérivés d'hydantoïne optiquement actifs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41917A DE1216879B (de) | 1964-02-05 | 1964-02-05 | Verfahren zur Herstellung von optisch aktiven Hydantoinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1216879B true DE1216879B (de) | 1966-05-18 |
Family
ID=7098862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF41917A Pending DE1216879B (de) | 1964-02-05 | 1964-02-05 | Verfahren zur Herstellung von optisch aktiven Hydantoinderivaten |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT250986B (enrdf_load_stackoverflow) |
| BE (1) | BE659315A (enrdf_load_stackoverflow) |
| CH (1) | CH439305A (enrdf_load_stackoverflow) |
| DE (1) | DE1216879B (enrdf_load_stackoverflow) |
| FR (1) | FR1425595A (enrdf_load_stackoverflow) |
| GB (1) | GB1039969A (enrdf_load_stackoverflow) |
| NL (1) | NL6501504A (enrdf_load_stackoverflow) |
-
1964
- 1964-02-05 DE DEF41917A patent/DE1216879B/de active Pending
-
1965
- 1965-02-03 CH CH146465A patent/CH439305A/de unknown
- 1965-02-04 AT AT98265A patent/AT250986B/de active
- 1965-02-05 NL NL6501504A patent/NL6501504A/xx unknown
- 1965-02-05 BE BE659315D patent/BE659315A/xx unknown
- 1965-02-05 FR FR4611A patent/FR1425595A/fr not_active Expired
- 1965-02-05 GB GB516665A patent/GB1039969A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| BE659315A (enrdf_load_stackoverflow) | 1965-08-05 |
| GB1039969A (en) | 1966-08-24 |
| AT250986B (de) | 1966-12-12 |
| CH439305A (de) | 1967-07-15 |
| NL6501504A (enrdf_load_stackoverflow) | 1965-08-06 |
| FR1425595A (fr) | 1966-01-24 |
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