SU565630A3 - Способ получени производных пиразола - Google Patents
Способ получени производных пиразолаInfo
- Publication number
- SU565630A3 SU565630A3 SU7502170651A SU2170651A SU565630A3 SU 565630 A3 SU565630 A3 SU 565630A3 SU 7502170651 A SU7502170651 A SU 7502170651A SU 2170651 A SU2170651 A SU 2170651A SU 565630 A3 SU565630 A3 SU 565630A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- methyl
- solution
- nitro
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 239000000243 solution Substances 0.000 claims 12
- -1 -butyl Chemical group 0.000 claims 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 239000000706 filtrate Substances 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 239000002244 precipitate Substances 0.000 claims 5
- 239000007787 solid Substances 0.000 claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 239000005457 ice water Substances 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- HGBWQGJWYQJSEA-UHFFFAOYSA-N 1-methyl-5-nitro-2-(2-phenylethenyl)imidazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=CC=2C=CC=CC=2)=N1 HGBWQGJWYQJSEA-UHFFFAOYSA-N 0.000 claims 2
- JLQLFVSTEDRFAD-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbaldehyde Chemical compound CN1C(C=O)=NC=C1[N+]([O-])=O JLQLFVSTEDRFAD-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 239000002274 desiccant Substances 0.000 claims 2
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 claims 2
- 239000000284 extract Substances 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 230000002140 halogenating effect Effects 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 239000010410 layer Substances 0.000 claims 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims 2
- 238000005949 ozonolysis reaction Methods 0.000 claims 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- ZWKTYLHETWULIP-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbonyl bromide Chemical compound CN1C(C(Br)=O)=NC=C1[N+]([O-])=O ZWKTYLHETWULIP-UHFFFAOYSA-N 0.000 claims 1
- 125000006023 1-pentenyl group Chemical group 0.000 claims 1
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 claims 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000006024 2-pentenyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- PTTXIGMAOLXWKO-UHFFFAOYSA-N 5-amino-1-(2-chloroethyl)-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NN(CCCl)C(N)=C1C#N PTTXIGMAOLXWKO-UHFFFAOYSA-N 0.000 claims 1
- SAUUKWGLDNIFRT-UHFFFAOYSA-N 5-amino-1-(2-hydroxyethyl)-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NN(CCO)C(N)=C1C#N SAUUKWGLDNIFRT-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 240000005979 Hordeum vulgare Species 0.000 claims 1
- 235000007340 Hordeum vulgare Nutrition 0.000 claims 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 239000002024 ethyl acetate extract Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003136 n-heptyl 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])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- 150000003217 pyrazoles Chemical class 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000004809 thin layer chromatography Methods 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38513673A | 1973-08-02 | 1973-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU565630A3 true SU565630A3 (ru) | 1977-07-15 |
Family
ID=23520163
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502170651A SU565630A3 (ru) | 1973-08-02 | 1975-09-04 | Способ получени производных пиразола |
| SU7502171154A SU582758A3 (ru) | 1973-08-02 | 1975-09-12 | Способ получени производных пиразола |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502171154A SU582758A3 (ru) | 1973-08-02 | 1975-09-12 | Способ получени производных пиразола |
Country Status (18)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014268700B2 (en) * | 2013-05-20 | 2018-07-05 | University Of Washington Through Its Center For Commercialization | 5-aminopyrazole-4-carboxamide inhibitors of CDPK1 from T. gondii and C. parvum |
-
1974
- 1974-06-18 ZA ZA00743887A patent/ZA743887B/xx unknown
- 1974-06-20 IL IL45073A patent/IL45073A/en unknown
- 1974-07-02 DE DE2431775A patent/DE2431775A1/de active Pending
- 1974-07-24 RO RO7400079581A patent/RO63973A/ro unknown
- 1974-07-25 NL NL7410033A patent/NL7410033A/xx unknown
- 1974-07-29 AR AR254925A patent/AR203854A1/es active
- 1974-07-29 DD DD180187A patent/DD112759A5/xx unknown
- 1974-07-31 AT AT627474A patent/AT337691B/de not_active IP Right Cessation
- 1974-08-01 BR BR6317/74A patent/BR7406317D0/pt unknown
- 1974-08-01 JP JP49088635A patent/JPS5047978A/ja active Pending
- 1974-08-01 SE SE7409957A patent/SE7409957L/xx unknown
- 1974-08-01 IT IT25881/74A patent/IT1049204B/it active
- 1974-08-01 DK DK410874A patent/DK410874A/da unknown
- 1974-08-02 BE BE1006105A patent/BE818417A/xx unknown
- 1974-08-02 ES ES428914A patent/ES428914A0/es active Pending
- 1974-08-02 PL PL1974192766A patent/PL96805B1/pl unknown
- 1974-08-02 PL PL1974173196A patent/PL91696B1/pl unknown
- 1974-08-02 PL PL1974192765A patent/PL96804B1/pl unknown
- 1974-08-02 FR FR7427017A patent/FR2240009A1/fr active Granted
- 1974-08-02 PL PL1974184214A patent/PL94238B1/pl unknown
- 1974-08-02 PL PL1974184215A patent/PL92429B1/pl unknown
-
1975
- 1975-01-01 AR AR257999A patent/AR205814A1/es active
- 1975-01-01 AR AR258000A patent/AR204130A1/es active
- 1975-09-04 SU SU7502170651A patent/SU565630A3/ru active
- 1975-09-12 SU SU7502171154A patent/SU582758A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| BE818417A (fr) | 1975-02-03 |
| AR205814A1 (es) | 1976-06-07 |
| ES428914A0 (es) | 1977-02-01 |
| PL92429B1 (enrdf_load_stackoverflow) | 1977-04-30 |
| RO63973A (fr) | 1978-09-15 |
| JPS5047978A (enrdf_load_stackoverflow) | 1975-04-28 |
| AT337691B (de) | 1977-07-11 |
| AR204130A1 (es) | 1975-11-20 |
| DD112759A5 (enrdf_load_stackoverflow) | 1975-05-05 |
| AU7052874A (en) | 1976-01-08 |
| BR7406317D0 (pt) | 1975-05-20 |
| ATA627474A (de) | 1976-11-15 |
| ZA743887B (en) | 1975-06-25 |
| IL45073A (en) | 1977-07-31 |
| IL45073A0 (en) | 1974-09-10 |
| PL96804B1 (pl) | 1978-01-31 |
| DK410874A (enrdf_load_stackoverflow) | 1975-04-01 |
| SE7409957L (enrdf_load_stackoverflow) | 1975-02-03 |
| PL91696B1 (enrdf_load_stackoverflow) | 1977-03-31 |
| IT1049204B (it) | 1981-01-20 |
| PL94238B1 (enrdf_load_stackoverflow) | 1977-07-30 |
| FR2240009A1 (en) | 1975-03-07 |
| AR203854A1 (es) | 1975-10-31 |
| PL96805B1 (pl) | 1978-01-31 |
| SU582758A3 (ru) | 1977-11-30 |
| FR2240009B1 (enrdf_load_stackoverflow) | 1978-07-28 |
| DE2431775A1 (de) | 1975-02-20 |
| NL7410033A (nl) | 1975-02-04 |
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