DE1288607B - Verfahren zur Herstellung von Benzoxazolderivaten - Google Patents
Verfahren zur Herstellung von BenzoxazolderivatenInfo
- Publication number
- DE1288607B DE1288607B DEC24612A DEC0024612A DE1288607B DE 1288607 B DE1288607 B DE 1288607B DE C24612 A DEC24612 A DE C24612A DE C0024612 A DEC0024612 A DE C0024612A DE 1288607 B DE1288607 B DE 1288607B
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- benzoxazole derivatives
- parts
- aminobenzoxazole
- general formula
- 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
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title claims description 4
- JPBLHOJFMBOCAF-UHFFFAOYSA-N 1,3-benzoxazol-2-amine Chemical compound C1=CC=C2OC(N)=NC2=C1 JPBLHOJFMBOCAF-UHFFFAOYSA-N 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000004202 carbamide Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
- 241001279009 Strychnos toxifera Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 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
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960005453 strychnine Drugs 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- YAXGBZDYGZBRBQ-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazol-2-amine Chemical compound NC1=NCCO1 YAXGBZDYGZBRBQ-UHFFFAOYSA-N 0.000 description 1
- DZWTXWPRWRLHIL-UHFFFAOYSA-N 6-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=C2N=C(N)SC2=C1 DZWTXWPRWRLHIL-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl radical Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL280954D NL280954A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1961-07-14 | ||
| DEC24612A DE1288607B (de) | 1961-07-14 | 1961-07-14 | Verfahren zur Herstellung von Benzoxazolderivaten |
| CH747962A CH445494A (de) | 1961-07-14 | 1962-06-21 | Verfahren zur Herstellung von Benzoxazolderivaten |
| US209213A US3162644A (en) | 1961-07-14 | 1962-07-11 | Nu-alkyl-2-benzoxazolyl urea compounds |
| GB27265/62A GB1008264A (en) | 1961-07-14 | 1962-07-16 | Benzoxazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC24612A DE1288607B (de) | 1961-07-14 | 1961-07-14 | Verfahren zur Herstellung von Benzoxazolderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1288607B true DE1288607B (de) | 1969-02-06 |
Family
ID=7017688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC24612A Pending DE1288607B (de) | 1961-07-14 | 1961-07-14 | Verfahren zur Herstellung von Benzoxazolderivaten |
Country Status (5)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3940261A1 (de) * | 1989-12-06 | 1991-06-13 | Agrolinz Agrarchemikalien Muen | Verfahren zur herstellung reiner, unsymmetrisch disubstituierter harnstoffe |
| US5099021A (en) * | 1989-11-10 | 1992-03-24 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Process for the preparation of pure, unsymmetrically disubstituted ureas |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1247318B (de) * | 1960-10-13 | 1967-08-17 | Albert Ag Chem Werke | Verfahren zur Herstellung von N-[5-Chlormethyloxazolinyl-(2)]-thioharnstoffderivaten |
| BE637819A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-09-29 | |||
| US3399987A (en) * | 1965-08-02 | 1968-09-03 | United States Borax Chem | 2-alkylaminobenzimidazoles as herbicides |
| GB1310224A (en) * | 1969-07-22 | 1973-03-14 | Lilly Industries Ltd | Oxazole thioureas |
| US4171364A (en) * | 1971-10-01 | 1979-10-16 | Eli Lilly And Company | N-heterocyclic ureas as immune regulants |
| CH601984A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-03-22 | 1978-07-14 | Hoffmann La Roche | |
| EP1678145A2 (en) * | 2003-10-28 | 2006-07-12 | Vertex Pharmaceuticals Incorporated | Benzimidazoles useful as modulators of ion channels |
| US7550499B2 (en) * | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| MX2007008434A (es) * | 2005-01-19 | 2007-07-25 | Squibb Bristol Myers Co | Derivados de 2-fenoxi-n-(1,3,4-tiadizol-2il)piridin-3-amina y compuestos relacionados como inhibidores del receptor p2y1 para el tratamiento de trastornos tromboembolicos. |
| WO2007002635A2 (en) * | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | C-linked cyclic antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
| WO2007002584A1 (en) | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | Linear urea mimics antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
| US7714002B2 (en) * | 2005-06-27 | 2010-05-11 | Bristol-Myers Squibb Company | Carbocycle and heterocycle antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| ATE505468T1 (de) * | 2005-06-27 | 2011-04-15 | Bristol Myers Squibb Co | N-gebundene heterocyclische antagonisten des p2y1-rezeptors zur behandlung von thromboseleiden |
| US7960569B2 (en) * | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| CN118812459A (zh) * | 2024-07-04 | 2024-10-22 | 四川省医学科学院·四川省人民医院 | 含苯并噻唑或苯并恶唑的化合物、其制备方法及其应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE566055A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| GB785628A (en) * | 1954-08-30 | 1957-10-30 | Mcneilab Inc | Improvements in or relating to the production of skeletal muscle relaxant comprising5-chlorobenzoxazoles |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2886572A (en) * | 1959-05-12 | Z-aminobenzoxazoles | ||
| US2780633A (en) * | 1957-02-05 | Method of making benzoxazole | ||
| US2073600A (en) * | 1933-12-30 | 1937-03-16 | Ig Farbenindustrie Ag | Heterocyclic hydrazines |
| US2148920A (en) * | 1936-02-28 | 1939-02-28 | Gen Aniline Works Inc | Process for producing compounds of the azole series |
| US2776977A (en) * | 1955-04-18 | 1957-01-08 | Monsanto Chemicals | Halogen substituted unsaturated azolyl ethers |
| US2737516A (en) * | 1955-05-02 | 1956-03-06 | Du Pont | Fluorescent whitening agents |
| US2756135A (en) * | 1955-07-13 | 1956-07-24 | Du Pont | 1-methyl-3-(2-benzothiazolyl)-ureas and their use as herbicides |
| US2895877A (en) * | 1956-07-30 | 1959-07-21 | Mcneilab Inc | Composition and method for relieving spasticity |
| US2806853A (en) * | 1956-07-31 | 1957-09-17 | Merck & Co Inc | Chemical compounds and processes for preparing the same |
| US3102074A (en) * | 1961-03-01 | 1963-08-27 | Merck & Co Inc | Anthelmintic compositions and method of employing same |
-
0
- NL NL280954D patent/NL280954A/xx unknown
-
1961
- 1961-07-14 DE DEC24612A patent/DE1288607B/de active Pending
-
1962
- 1962-06-21 CH CH747962A patent/CH445494A/de unknown
- 1962-07-11 US US209213A patent/US3162644A/en not_active Expired - Lifetime
- 1962-07-16 GB GB27265/62A patent/GB1008264A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE566055A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| GB785628A (en) * | 1954-08-30 | 1957-10-30 | Mcneilab Inc | Improvements in or relating to the production of skeletal muscle relaxant comprising5-chlorobenzoxazoles |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5099021A (en) * | 1989-11-10 | 1992-03-24 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Process for the preparation of pure, unsymmetrically disubstituted ureas |
| DE3940261A1 (de) * | 1989-12-06 | 1991-06-13 | Agrolinz Agrarchemikalien Muen | Verfahren zur herstellung reiner, unsymmetrisch disubstituierter harnstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| NL280954A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| CH445494A (de) | 1967-10-31 |
| US3162644A (en) | 1964-12-22 |
| GB1008264A (en) | 1965-10-27 |
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