DE1795821C2 - Verfahren zur Herstellung von 3-Hydroxyisoxazolen - Google Patents
Verfahren zur Herstellung von 3-HydroxyisoxazolenInfo
- Publication number
- DE1795821C2 DE1795821C2 DE1795821A DE1795821A DE1795821C2 DE 1795821 C2 DE1795821 C2 DE 1795821C2 DE 1795821 A DE1795821 A DE 1795821A DE 1795821 A DE1795821 A DE 1795821A DE 1795821 C2 DE1795821 C2 DE 1795821C2
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- reaction
- solution
- ether
- hydroxyisoxazoles
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 23
- FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical class OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
- -1 η-butyl Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- 239000000203 mixture Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- IRJCBFDCFXCWGO-SCSAIBSYSA-N (2r)-2-azaniumyl-2-(3-oxo-1,2-oxazol-5-yl)acetate Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC(=O)NO1 IRJCBFDCFXCWGO-SCSAIBSYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IRJCBFDCFXCWGO-UHFFFAOYSA-N Ibotenic acid Natural products OC(=O)C(N)C1=CC(=O)NO1 IRJCBFDCFXCWGO-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- CKRYUEGQFBCEFH-UHFFFAOYSA-N 4,4-diethoxybut-2-ynoic acid Chemical compound CCOC(OCC)C#CC(O)=O CKRYUEGQFBCEFH-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UBMXBBULKSCXLZ-UHFFFAOYSA-N OC1=CC=NO1 Chemical class OC1=CC=NO1 UBMXBBULKSCXLZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- OOIQFSUYMNZCLM-UHFFFAOYSA-N ethyl 4,4-diethoxybut-2-ynoate Chemical compound CCOC(OCC)C#CC(=O)OCC OOIQFSUYMNZCLM-UHFFFAOYSA-N 0.000 description 2
- FCJJZKCJURDYNF-UHFFFAOYSA-N ethyl but-2-ynoate Chemical compound CCOC(=O)C#CC FCJJZKCJURDYNF-UHFFFAOYSA-N 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- NSCBMBLDRBRNFA-UHFFFAOYSA-N 3-methoxy-5-phenyl-1,2-oxazole Chemical compound O1N=C(OC)C=C1C1=CC=CC=C1 NSCBMBLDRBRNFA-UHFFFAOYSA-N 0.000 description 1
- MTVFKTPLKNPKCM-UHFFFAOYSA-N 3-oxo-1,2-oxazole-5-carbaldehyde Chemical compound OC=1C=C(C=O)ON=1 MTVFKTPLKNPKCM-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- GKRIFEXGXVBLEA-UHFFFAOYSA-N 5-(2-methylpropyl)-1,2-oxazol-3-one Chemical compound CC(C)CC1=CC(=O)NO1 GKRIFEXGXVBLEA-UHFFFAOYSA-N 0.000 description 1
- LTBAGKFPRMPHKH-UHFFFAOYSA-N 5-(diethoxymethyl)-1,2-oxazol-3-one Chemical compound CCOC(OCC)C1=CC(=O)NO1 LTBAGKFPRMPHKH-UHFFFAOYSA-N 0.000 description 1
- COJOQIBKKJIHLX-UHFFFAOYSA-N 5-butyl-1,2-oxazol-3-one Chemical compound CCCCC1=CC(=O)NO1 COJOQIBKKJIHLX-UHFFFAOYSA-N 0.000 description 1
- POQFFIGGQLBQNN-UHFFFAOYSA-N 5-decyl-1,2-oxazol-3-one Chemical compound CCCCCCCCCCC1=CC(=O)NO1 POQFFIGGQLBQNN-UHFFFAOYSA-N 0.000 description 1
- COJBJDILSDCGSL-UHFFFAOYSA-N 5-ethyl-1,2-oxazol-3-one Chemical compound CCC1=CC(=O)NO1 COJBJDILSDCGSL-UHFFFAOYSA-N 0.000 description 1
- AFVFIJAYAFTQRB-UHFFFAOYSA-N 5-phenylisoxazol-3-ol Chemical compound O1N=C(O)C=C1C1=CC=CC=C1 AFVFIJAYAFTQRB-UHFFFAOYSA-N 0.000 description 1
- WKKVFNUVMXLZDZ-UHFFFAOYSA-N 5-propan-2-yl-1,2-oxazol-3-one Chemical compound CC(C)C1=CC(=O)NO1 WKKVFNUVMXLZDZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ACJOYTKWHPEIHW-UHFFFAOYSA-N ethyl 3-phenylprop-2-ynoate Chemical compound CCOC(=O)C#CC1=CC=CC=C1 ACJOYTKWHPEIHW-UHFFFAOYSA-N 0.000 description 1
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JIRJHEXNDQBKRZ-UHFFFAOYSA-N phosgene oxime Chemical compound ON=C(Cl)Cl JIRJHEXNDQBKRZ-UHFFFAOYSA-N 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- IJNJLGFTSIAHEA-UHFFFAOYSA-N prop-2-ynal Chemical compound O=CC#C IJNJLGFTSIAHEA-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/12—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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5251564 | 1964-09-14 | ||
| JP3482865 | 1965-06-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1795821B1 DE1795821B1 (de) | 1980-07-17 |
| DE1795821C2 true DE1795821C2 (de) | 1981-04-02 |
Family
ID=26373685
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1795821A Expired DE1795821C2 (de) | 1964-09-14 | 1965-09-13 | Verfahren zur Herstellung von 3-Hydroxyisoxazolen |
| DE1620306A Expired DE1620306C3 (de) | 1964-09-14 | 1965-09-13 | 3-Hydroxy-5-alkylisoxazole |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1620306A Expired DE1620306C3 (de) | 1964-09-14 | 1965-09-13 | 3-Hydroxy-5-alkylisoxazole |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US3544584A (OSRAM) |
| BR (1) | BR6573114D0 (OSRAM) |
| CH (1) | CH451153A (OSRAM) |
| DE (2) | DE1795821C2 (OSRAM) |
| GB (1) | GB1113618A (OSRAM) |
| IT (1) | IT974507B (OSRAM) |
| NL (2) | NL6511925A (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5033064B2 (OSRAM) * | 1971-10-23 | 1975-10-27 | ||
| JPS5031039A (OSRAM) * | 1973-07-27 | 1975-03-27 | ||
| JPS5498325A (en) * | 1978-01-19 | 1979-08-03 | Nippon Kayaku Co Ltd | Agricultural and horticultural fungicidal composition |
| DK150615C (da) * | 1982-10-26 | 1987-11-09 | Cheminova As | Fremgangsmaade til fremstilling af substituerede 3-isoxazololer |
| JPS59190977A (ja) * | 1983-04-12 | 1984-10-29 | Sankyo Co Ltd | ３−ヒドロキシ−５−メチルイソオキサゾ−ルの連続製法 |
| US4593024A (en) * | 1985-08-15 | 1986-06-03 | International Minerals & Chemical Corp. | Dihydroisoxazole compounds and anthelmintic use |
| US4636517A (en) * | 1985-10-18 | 1987-01-13 | International Minerals & Chemical Corp. | 3-tolylthio-4-amino-4,5-dihydro isoxazole as anthelmintic |
| IL105577A (en) * | 1992-05-07 | 1997-09-30 | Sankyo Co | Fungicidal compositions containing 3-hydroxy- 5-methylisoxazole or salts thereof, methods for the preparation thereof and their use |
| KR101535324B1 (ko) * | 2010-03-16 | 2015-07-08 | 닛뽕소다 가부시키가이샤 | 식물 병해 방제제 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH427803A (de) * | 1963-12-06 | 1967-01-15 | Geigy Ag J R | Verfahren zur Herstellung eines neuen Isoxazolderivates |
-
0
- NL NL130992D patent/NL130992C/xx active
-
1965
- 1965-09-07 IT IT19947/65A patent/IT974507B/it active
- 1965-09-13 DE DE1795821A patent/DE1795821C2/de not_active Expired
- 1965-09-13 CH CH1267165A patent/CH451153A/de unknown
- 1965-09-13 DE DE1620306A patent/DE1620306C3/de not_active Expired
- 1965-09-14 NL NL6511925A patent/NL6511925A/xx unknown
- 1965-09-14 GB GB39288/65A patent/GB1113618A/en not_active Expired
- 1965-09-14 BR BR173114/65A patent/BR6573114D0/pt unknown
-
1968
- 1968-10-01 US US767053A patent/US3544584A/en not_active Expired - Lifetime
-
1970
- 1970-03-05 US US26460A patent/US3687968A/en not_active Expired - Lifetime
Non-Patent Citations (2)
| Title |
|---|
| Proceedings Chem. Soc., 1961, S. 387-388 * |
| Weissberger, A.: The Chemistry of Heterocyclic Compounds, Bd. 17, 1962, S. 118-121 u. S. 151 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620306B2 (de) | 1977-08-11 |
| NL6511925A (OSRAM) | 1966-03-15 |
| DE1620306C3 (de) | 1978-04-20 |
| US3687968A (en) | 1972-08-29 |
| CH451153A (de) | 1968-05-15 |
| IT974507B (it) | 1974-07-10 |
| GB1113618A (en) | 1968-05-15 |
| BR6573114D0 (pt) | 1973-09-11 |
| DE1795821B1 (de) | 1980-07-17 |
| NL130992C (OSRAM) | |
| US3544584A (en) | 1970-12-01 |
| DE1620306A1 (de) | 1970-03-12 |
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