NO133663B - - Google Patents
Download PDFInfo
- Publication number
- NO133663B NO133663B NO327871A NO327871A NO133663B NO 133663 B NO133663 B NO 133663B NO 327871 A NO327871 A NO 327871A NO 327871 A NO327871 A NO 327871A NO 133663 B NO133663 B NO 133663B
- Authority
- NO
- Norway
- Prior art keywords
- mol
- added
- ether
- water
- heated
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 5
- PQWGFUFROKIJBO-UHFFFAOYSA-N 1-(3-chlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(Cl)=C1 PQWGFUFROKIJBO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
- -1 Sulfuryl- Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
- RPMOHVRRKYJFSB-UHFFFAOYSA-N 1-(3-fluorophenyl)propan-1-one Chemical class CCC(=O)C1=CC=CC(F)=C1 RPMOHVRRKYJFSB-UHFFFAOYSA-N 0.000 description 1
- AXCPQHPNAZONTH-UHFFFAOYSA-N 2-chloro-1-phenylpropan-1-one Chemical compound CC(Cl)C(=O)C1=CC=CC=C1 AXCPQHPNAZONTH-UHFFFAOYSA-N 0.000 description 1
- WBUOVKBZJOIOAE-UHFFFAOYSA-N 3-chlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1 WBUOVKBZJOIOAE-UHFFFAOYSA-N 0.000 description 1
- JZTPKAROPNTQQV-UHFFFAOYSA-N 3-fluorobenzonitrile Chemical compound FC1=CC=CC(C#N)=C1 JZTPKAROPNTQQV-UHFFFAOYSA-N 0.000 description 1
- HEYVINCGKDONRU-UHFFFAOYSA-N Bupropion hydrochloride Chemical compound Cl.CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 HEYVINCGKDONRU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO327871A NO133663C (enrdf_load_stackoverflow) | 1969-12-04 | 1971-09-02 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5923169 | 1969-12-04 | ||
| NO4645/70A NO131127C (enrdf_load_stackoverflow) | 1969-12-04 | 1970-12-03 | |
| NO327871A NO133663C (enrdf_load_stackoverflow) | 1969-12-04 | 1971-09-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133663B true NO133663B (enrdf_load_stackoverflow) | 1976-03-01 |
| NO133663C NO133663C (enrdf_load_stackoverflow) | 1976-06-09 |
Family
ID=27260499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO327871A NO133663C (enrdf_load_stackoverflow) | 1969-12-04 | 1971-09-02 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO133663C (enrdf_load_stackoverflow) |
-
1971
- 1971-09-02 NO NO327871A patent/NO133663C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO133663C (enrdf_load_stackoverflow) | 1976-06-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Djerassi et al. | Brominations with pyridine hydrobromide perbromide | |
| DE2814556C2 (de) | Substituierte Phenylessigsäurederivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen | |
| NO131127B (enrdf_load_stackoverflow) | ||
| Brown et al. | Synthesis of porphyrinogen-like compounds (mixed quaterenes) | |
| JPS62187440A (ja) | ４−アミノヘキセ−５−エン酸の製法 | |
| DE2437882C3 (de) | Verfahren zur Herstellung von Estern des 3-Phenoxybenzylalkohols | |
| Galat | The Preparation of 2, 4, 5-Trichlorophenoxyacetic Acid (2, 4, 5-T) | |
| EP0560109A2 (de) | Verfahren zur Herstellung von 1-Fluorcyclopropyl-methyl-keton | |
| BERGMANN et al. | Di (p-chlorophenyl) trichloromethylcarbinol and related compounds | |
| NO133663B (enrdf_load_stackoverflow) | ||
| Cason et al. | Preparation of Pure Secondary Bromides | |
| NO149353B (no) | Fremgangsmaate ved fremstilling av 6-klor-alfa-metylkarbazol-2-eddiksyre | |
| Timmermans et al. | Pyrazoles XI. The synthesis of 1, 1′‐dimethylbipyrazolyls | |
| US2218349A (en) | Halogenated derivatives of aceto propyl alcohol | |
| Sunde et al. | The separation of the isomeric dinitro-1, 4-dibromobenzenes and their reactions with p-phenylenediamine | |
| Chupp et al. | Active heteromethylene compounds. 2. A new synthesis of N-(halomethyl) acylamides | |
| Dreiding et al. | The Structure of the Solid Product from the Condensation of Methyl γ-Bromocrotonate with Sodium Methoxide1 | |
| US4339593A (en) | Process for the manufacture of 3,6-dialkyl resorcylic acid esters | |
| CN1058960C (zh) | 新型植物生长调节剂三氟吲哚丁酸或其衍生物的合成 | |
| US2302671A (en) | Halogenated derivatives of aceto propane | |
| Snyder et al. | Amine Replacement Reactions of α-Dimethylaminomethyl-β-methoxynaphthalene | |
| Jackson | 3-(p-Methoxyphenoxy)-2, 6-dinitrobenzaldehyde and Two of Its Derivatives | |
| US4220792A (en) | 1-Phenyl-pyrazole derivatives | |
| Farmer et al. | CCCXXI.—The formation and stability of associated alicyclic systems. Part II. The formation and disruption of dicyclic dihydroresorcinols | |
| Lutz et al. | Dibenzoylethylene Oxide and Chlorohydrin |