SU692560A3 - Способ получени производных тиазола - Google Patents
Способ получени производных тиазолаInfo
- Publication number
- SU692560A3 SU692560A3 SU762319294A SU2319294A SU692560A3 SU 692560 A3 SU692560 A3 SU 692560A3 SU 762319294 A SU762319294 A SU 762319294A SU 2319294 A SU2319294 A SU 2319294A SU 692560 A3 SU692560 A3 SU 692560A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- methyl
- formula
- concentrated
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- 150000007979 thiazole derivatives Chemical class 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- 239000000047 product Substances 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 8
- 239000000243 solution Substances 0.000 claims 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 8
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- -1 tetrahydrofsfane Chemical compound 0.000 claims 5
- DXWAMOUMQYPGDC-UHFFFAOYSA-N 3-(2-methyl-1,3-thiazol-5-yl)propanoic acid Chemical compound CC1=NC=C(CCC(O)=O)S1 DXWAMOUMQYPGDC-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000000908 ammonium hydroxide Substances 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000004494 ethyl ester group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000012044 organic layer Substances 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000000284 extract Substances 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000002329 infrared spectrum Methods 0.000 claims 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims 2
- 239000002609 medium Substances 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- DVFWNODYANYNMC-UHFFFAOYSA-N 2-(2-methyl-1,3-thiazol-5-yl)acetic acid Chemical compound CC1=NC=C(CC(O)=O)S1 DVFWNODYANYNMC-UHFFFAOYSA-N 0.000 claims 1
- AQEOOPRSWRSWNF-UHFFFAOYSA-N 2-(2-propyl-1,3-thiazol-5-yl)acetic acid Chemical compound CCCC1=NC=C(CC(O)=O)S1 AQEOOPRSWRSWNF-UHFFFAOYSA-N 0.000 claims 1
- NSPDLMCVVUUTDU-UHFFFAOYSA-N 3-(2-methyl-1,3-thiazol-5-yl)prop-2-enoic acid Chemical compound CC1=NC=C(C=CC(O)=O)S1 NSPDLMCVVUUTDU-UHFFFAOYSA-N 0.000 claims 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 claims 1
- PZTGZYPQSNTBDO-UHFFFAOYSA-N CCC(C(Br)C=O)C(O)=O Chemical compound CCC(C(Br)C=O)C(O)=O PZTGZYPQSNTBDO-UHFFFAOYSA-N 0.000 claims 1
- 229920000742 Cotton Polymers 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- FVELDMCOCLJSQN-UHFFFAOYSA-N benzene;1,1-dichloroethane Chemical compound CC(Cl)Cl.C1=CC=CC=C1 FVELDMCOCLJSQN-UHFFFAOYSA-N 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
- 239000012043 crude product Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- SQYPHZPZGJWWEJ-UHFFFAOYSA-N ethyl 2-(2-propyl-1,3-thiazol-5-yl)acetate Chemical compound CCCC1=NC=C(CC(=O)OCC)S1 SQYPHZPZGJWWEJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000010898 silica gel chromatography Methods 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 1
- 235000010269 sulphur dioxide Nutrition 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7538061A FR2334353A1 (fr) | 1975-12-12 | 1975-12-12 | Nouveaux derives thiazoliques, un procede pour leur preparation et leur application comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU692560A3 true SU692560A3 (ru) | 1979-10-15 |
Family
ID=9163662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762319294A SU692560A3 (ru) | 1975-12-12 | 1976-02-10 | Способ получени производных тиазола |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4053618A (enExample) |
| AT (1) | AT348516B (enExample) |
| FR (1) | FR2334353A1 (enExample) |
| IE (1) | IE42776B1 (enExample) |
| SU (1) | SU692560A3 (enExample) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130759C (enExample) * | 1965-10-07 | |||
| FR2265370B2 (enExample) * | 1974-03-26 | 1977-12-02 | Roussel Uclaf | |
| US3882110A (en) * | 1969-06-11 | 1975-05-06 | Roussel Uclaf | Novel 2-alkyl-5-thiazole-carboxylic acid derivatives |
-
1975
- 1975-12-12 FR FR7538061A patent/FR2334353A1/fr active Granted
-
1976
- 1976-02-02 US US05/654,514 patent/US4053618A/en not_active Expired - Lifetime
- 1976-02-10 SU SU762319294A patent/SU692560A3/ru active
- 1976-02-12 AT AT99376A patent/AT348516B/de not_active IP Right Cessation
- 1976-02-13 IE IE297/76A patent/IE42776B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4053618A (en) | 1977-10-11 |
| FR2334353B1 (enExample) | 1978-07-28 |
| IE42776L (en) | 1977-06-12 |
| FR2334353A1 (fr) | 1977-07-08 |
| ATA99376A (de) | 1978-07-15 |
| AT348516B (de) | 1979-02-26 |
| IE42776B1 (en) | 1980-10-22 |
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