SU577992A3 - Способ получени производных бензоксазола - Google Patents
Способ получени производных бензоксазолаInfo
- Publication number
- SU577992A3 SU577992A3 SU7402074061A SU2074061A SU577992A3 SU 577992 A3 SU577992 A3 SU 577992A3 SU 7402074061 A SU7402074061 A SU 7402074061A SU 2074061 A SU2074061 A SU 2074061A SU 577992 A3 SU577992 A3 SU 577992A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- solution
- water
- washed
- evaporated
- ether
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 5
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 48
- 239000000243 solution Substances 0.000 claims 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 24
- 235000011121 sodium hydroxide Nutrition 0.000 claims 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 12
- 239000003921 oil Substances 0.000 claims 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 10
- -1 4-fluorobenzyl-5-benzoxazolyl propionic acid Chemical compound 0.000 claims 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 235000019260 propionic acid Nutrition 0.000 claims 6
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 6
- 235000011152 sodium sulphate Nutrition 0.000 claims 6
- 238000001704 evaporation Methods 0.000 claims 5
- 230000008020 evaporation Effects 0.000 claims 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- 238000003756 stirring Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 3
- 239000012259 ether extract Substances 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- 239000008096 xylene Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000002026 chloroform extract Substances 0.000 claims 2
- 239000006071 cream Substances 0.000 claims 2
- LPHWCEHIGYXCSG-UHFFFAOYSA-N ethyl 2-(3-amino-4-hydroxyphenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=C(O)C(N)=C1 LPHWCEHIGYXCSG-UHFFFAOYSA-N 0.000 claims 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 238000004809 thin layer chromatography Methods 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- AORZHWTVQQFEEI-UHFFFAOYSA-N (4-chlorophenyl) 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC1=CC=C(Cl)C=C1 AORZHWTVQQFEEI-UHFFFAOYSA-N 0.000 claims 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 claims 1
- SFAILOOQFZNOAU-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetic acid Chemical compound OC(=O)CC1=C(Cl)C=CC=C1Cl SFAILOOQFZNOAU-UHFFFAOYSA-N 0.000 claims 1
- MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 241000400611 Eucalyptus deanei Species 0.000 claims 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 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000012230 colorless oil Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- AUPFUMIGGADXGA-UHFFFAOYSA-N ethyl 2-(2-sulfanylidene-3h-1,3-benzoxazol-5-yl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=C2OC(=S)NC2=C1 AUPFUMIGGADXGA-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 150000004767 nitrides Chemical group 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 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
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB49260/73A GB1491863A (en) | 1973-10-23 | 1973-10-23 | 2,5-or 2,6-disubstituted benzoxazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU577992A3 true SU577992A3 (ru) | 1977-10-25 |
Family
ID=10451725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402074061A SU577992A3 (ru) | 1973-10-23 | 1974-10-22 | Способ получени производных бензоксазола |
Country Status (22)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2434003C2 (ru) * | 2006-05-11 | 2011-11-20 | Санофи-Авентис | Фениламинобензоксазолзамещенные карбоновые кислоты, способ их получения и их применение в качестве лекарственных средств |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1435721A (en) * | 1972-05-18 | 1976-05-12 | Lilly Industries Ltd | Benzoxazole derivatives |
| US3888864A (en) | 1973-06-29 | 1975-06-10 | Hoffmann La Roche | Amino lower alkyl ether derivatives of opium alkaloids |
| IT1099589B (it) * | 1978-08-04 | 1985-09-18 | Ravizza Spa | Processo per la preparazione di derivati dell'acido benzoxazolil propionico |
| IT1157295B (it) * | 1982-07-19 | 1987-02-11 | Ravizza Spa | Processo perfezionato per la preparazione di derivati dell'acido benzoxazolil propionico |
| JPH03173874A (ja) * | 1989-09-29 | 1991-07-29 | Mitsubishi Kasei Corp | 新規複素環化合物 |
-
1973
- 1973-10-23 GB GB49260/73A patent/GB1491863A/en not_active Expired
-
1974
- 1974-01-01 AR AR256198A patent/AR207232A1/es active
- 1974-10-04 ZA ZA00746341A patent/ZA746341B/xx unknown
- 1974-10-11 IL IL45837A patent/IL45837A/xx unknown
- 1974-10-16 CS CS747094A patent/CS188927B2/cs unknown
- 1974-10-21 BG BG028005A patent/BG26197A3/xx unknown
- 1974-10-22 IE IE2168/74A patent/IE40080B1/xx unknown
- 1974-10-22 BE BE6044793A patent/BE821350A/xx unknown
- 1974-10-22 NL NL7413788A patent/NL7413788A/xx not_active Application Discontinuation
- 1974-10-22 DK DK552774A patent/DK552774A/da unknown
- 1974-10-22 AT AT849374A patent/AT341519B/de not_active IP Right Cessation
- 1974-10-22 HU HULI265A patent/HU170452B/hu unknown
- 1974-10-22 SU SU7402074061A patent/SU577992A3/ru active
- 1974-10-22 CA CA212,029A patent/CA1038393A/en not_active Expired
- 1974-10-22 FR FR7435407A patent/FR2248039B1/fr not_active Expired
- 1974-10-22 RO RO7480290A patent/RO72841A/ro unknown
- 1974-10-22 DE DE19742450042 patent/DE2450042A1/de not_active Withdrawn
- 1974-10-22 CH CH1414374A patent/CH605863A5/xx not_active IP Right Cessation
- 1974-10-23 SE SE7413352A patent/SE7413352L/xx unknown
- 1974-10-23 JP JP49122355A patent/JPS5070362A/ja active Pending
- 1974-10-23 PL PL1974175042A patent/PL94057B1/pl unknown
- 1974-10-23 DD DD181873A patent/DD114609A5/xx unknown
-
1975
- 1975-01-01 AR AR259897A patent/AR207369A1/es active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2434003C2 (ru) * | 2006-05-11 | 2011-11-20 | Санофи-Авентис | Фениламинобензоксазолзамещенные карбоновые кислоты, способ их получения и их применение в качестве лекарственных средств |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA849374A (de) | 1977-06-15 |
| AT341519B (de) | 1978-02-10 |
| DE2450042A1 (de) | 1975-04-24 |
| AR207232A1 (es) | 1976-09-22 |
| FR2248039B1 (enrdf_load_stackoverflow) | 1978-07-28 |
| DD114609A5 (enrdf_load_stackoverflow) | 1975-08-12 |
| PL94057B1 (enrdf_load_stackoverflow) | 1977-07-30 |
| CH605863A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| ZA746341B (en) | 1976-06-30 |
| FR2248039A1 (enrdf_load_stackoverflow) | 1975-05-16 |
| CA1038393A (en) | 1978-09-12 |
| IE40080B1 (en) | 1979-03-14 |
| JPS5070362A (enrdf_load_stackoverflow) | 1975-06-11 |
| BE821350A (fr) | 1975-04-22 |
| BG26197A3 (bg) | 1979-02-15 |
| DK552774A (enrdf_load_stackoverflow) | 1975-06-16 |
| RO72841A (ro) | 1982-05-10 |
| AU7454674A (en) | 1976-04-29 |
| HU170452B (enrdf_load_stackoverflow) | 1977-06-28 |
| GB1491863A (en) | 1977-11-16 |
| CS188927B2 (en) | 1979-03-30 |
| NL7413788A (nl) | 1975-04-25 |
| IE40080L (en) | 1975-04-23 |
| IL45837A (en) | 1978-03-10 |
| AR207369A1 (es) | 1976-09-30 |
| IL45837A0 (en) | 1974-12-31 |
| SE7413352L (enrdf_load_stackoverflow) | 1975-04-24 |
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