SU413676A3 - - Google Patents
Info
- Publication number
- SU413676A3 SU413676A3 SU1222279A SU1222279A SU413676A3 SU 413676 A3 SU413676 A3 SU 413676A3 SU 1222279 A SU1222279 A SU 1222279A SU 1222279 A SU1222279 A SU 1222279A SU 413676 A3 SU413676 A3 SU 413676A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- methyl
- hydrochloride
- mixture
- recrystallization
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000203 mixture Chemical class 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- -1 4-pyrazolyl residue Chemical group 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 229930040373 Paraformaldehyde Natural products 0.000 description 7
- 229920002866 paraformaldehyde Polymers 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 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 5
- 238000010992 reflux Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- QBNRQCHCKIIYGV-UHFFFAOYSA-N 5-propyl-1h-pyrazole Chemical compound CCCC1=CC=NN1 QBNRQCHCKIIYGV-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- FZEDJUVQMGBVRC-UHFFFAOYSA-N 1-(5-methyl-1-phenylpyrazol-4-yl)ethanone Chemical compound CC1=C(C(=O)C)C=NN1C1=CC=CC=C1 FZEDJUVQMGBVRC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- HAKSOKWVNPZVNM-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine;hydrochloride Chemical compound Cl.C1CNC=CC1 HAKSOKWVNPZVNM-UHFFFAOYSA-N 0.000 description 1
- BVLUILUENLVAGB-UHFFFAOYSA-N 1-[1-(5-bromopyridin-2-yl)-5-methylpyrazol-4-yl]ethanone Chemical compound CC1=C(C(=O)C)C=NN1C1=CC=C(Br)C=N1 BVLUILUENLVAGB-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- POGWXTJNUCZEPR-UHFFFAOYSA-N 4-phenyl-1,2,3,6-tetrahydropyridin-1-ium;chloride Chemical compound Cl.C1NCCC(C=2C=CC=CC=2)=C1 POGWXTJNUCZEPR-UHFFFAOYSA-N 0.000 description 1
- CQPHZBOPSZGTJM-UHFFFAOYSA-N 4-phenylpiperidin-1-ium-4-carbonitrile;chloride Chemical compound Cl.C=1C=CC=CC=1C1(C#N)CCNCC1 CQPHZBOPSZGTJM-UHFFFAOYSA-N 0.000 description 1
- NNRLBUOQBHTARV-UHFFFAOYSA-N 5-phenyl-1h-pyrazole;hydrochloride Chemical compound Cl.N1N=CC=C1C1=CC=CC=C1 NNRLBUOQBHTARV-UHFFFAOYSA-N 0.000 description 1
- FIFOCEFOCMXMKA-UHFFFAOYSA-N 6-ethoxyhex-5-ene-2,4-dione Chemical compound CCOC=CC(=O)CC(C)=O FIFOCEFOCMXMKA-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH297567A CH535777A (de) | 1967-03-01 | 1967-03-01 | Verfahren zur Herstellung neuer azacycloaliphatischer Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU413676A3 true SU413676A3 (enrdf_load_stackoverflow) | 1974-01-30 |
Family
ID=4245835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1222279A SU413676A3 (enrdf_load_stackoverflow) | 1967-03-01 | 1968-02-28 |
Country Status (2)
| Country | Link |
|---|---|
| PL (1) | PL79288B1 (enrdf_load_stackoverflow) |
| SU (1) | SU413676A3 (enrdf_load_stackoverflow) |
-
1968
- 1968-02-28 SU SU1222279A patent/SU413676A3/ru active
- 1968-02-29 PL PL12553968A patent/PL79288B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL79288B1 (enrdf_load_stackoverflow) | 1975-06-30 |
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