BE564597A - - Google Patents
Info
- Publication number
- BE564597A BE564597A BE564597DA BE564597A BE 564597 A BE564597 A BE 564597A BE 564597D A BE564597D A BE 564597DA BE 564597 A BE564597 A BE 564597A
- Authority
- BE
- Belgium
- Prior art keywords
- alkenyl
- ether
- formula
- acid
- reacted
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 78
- 239000002253 acid Substances 0.000 claims description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 21
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 19
- 235000011152 sodium sulphate Nutrition 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 8
- -1 α-propargylthio-isobutyryl chloride Chemical compound 0.000 claims description 8
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005466 alkylenyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 230000000875 corresponding Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
- 230000002936 tranquilizing Effects 0.000 claims 1
- 239000003204 tranquilizing agent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- YWAKXRMUMFPDSH-UHFFFAOYSA-N Pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- CRPTXKKKIGGDBX-UHFFFAOYSA-N (Z)-but-2-ene Chemical group [CH2]C=CC CRPTXKKKIGGDBX-UHFFFAOYSA-N 0.000 description 2
- AVMHMVJVHYGDOO-UHFFFAOYSA-N 1-bromobut-2-ene Chemical compound CC=CCBr AVMHMVJVHYGDOO-UHFFFAOYSA-N 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N Allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N Propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000630 rising Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 1
- 229960000716 TONICS Drugs 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 230000002921 anti-spasmodic Effects 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001624 sedative Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000001256 tonic Effects 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE564597A true BE564597A (de) |
Family
ID=185408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE564597D BE564597A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE564597A (de) |
-
0
- BE BE564597D patent/BE564597A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE564597A (de) | ||
| EP0091851A1 (de) | Verfahren zur Herstellung von Arylethern, deren beide aromatischen Kerne verschiedene Substituenten tragen | |
| CH616659A5 (de) | ||
| CH407087A (fr) | Procédé de préparation de nouveaux dérivés de la diphénylacétamide | |
| EP0868419A1 (de) | Verfahren zur herstellung von n,n-dimethyl-n'-phenyl-harnstoff | |
| FR2505327A1 (fr) | Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues | |
| EP0625973B1 (de) | Verfahren zur herstellung von 2-amino-4-nitrobenzothiazol-derivaten und zwischenprodukte | |
| EP0228356B1 (de) | Hydroxy-4-indol-Derivate, Verfahren zur Herstellung und ihre Anwendung | |
| CH332334A (fr) | Procédé de fabrication de N-benzhydryl-N'-benzylpipérazines | |
| BE541651A (de) | ||
| FR2754255A1 (fr) | Procede de preparation de derives de trans-4-(4- aminomethylphenyl) cyclohexanols | |
| BE533436A (de) | ||
| CH627163A5 (en) | Processes for the preparation of new indole derivatives | |
| CH420107A (fr) | Procédé de préparation de nouveaux dérivés d'aralcoylaminoalcoylcyclohexanes substitués | |
| BE614417A (de) | ||
| WO2001072739A1 (fr) | Procede de preparation de composes 3-(4-hydroxy-1h-indol-5-ylmethyl)-pyridinium en passant par des enones | |
| BE610353A (de) | ||
| WO2001074803A1 (fr) | Procede de preparation de composes 3-(4-hydroxy-1h-indol-ylmethyl)-pyridiniums utilisant une reaction d'aldolisation | |
| BE451559A (de) | ||
| CH422762A (fr) | Procédé de préparation d'esters d'acides di-tert-butyl-naphtalène-4-sulfonique | |
| BE567029A (de) | ||
| CH316158A (fr) | Procédé de préparation d'oxazinones | |
| BE517991A (de) | ||
| BE517234A (de) | ||
| CH438318A (fr) | Procédé de préparation de nouvelles pyrrolobenzothiazines substituées |