NO132666B - - Google Patents
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- Publication number
- NO132666B NO132666B NO498/73A NO49873A NO132666B NO 132666 B NO132666 B NO 132666B NO 498/73 A NO498/73 A NO 498/73A NO 49873 A NO49873 A NO 49873A NO 132666 B NO132666 B NO 132666B
- Authority
- NO
- Norway
- Prior art keywords
- solution
- residue
- group
- hydrazine
- distilled
- Prior art date
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- -1 aliphatic oxo compound Chemical class 0.000 claims description 33
- 125000002252 acyl group Chemical group 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000002429 hydrazines Chemical class 0.000 claims description 18
- 125000001118 alkylidene group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 150000007857 hydrazones Chemical class 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 132
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 108
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 88
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
- 238000001816 cooling Methods 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 25
- 235000019341 magnesium sulphate Nutrition 0.000 description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 25
- 238000003756 stirring Methods 0.000 description 25
- 238000001914 filtration Methods 0.000 description 23
- 238000001035 drying Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 229940072033 potash Drugs 0.000 description 19
- 235000015320 potassium carbonate Nutrition 0.000 description 19
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 11
- 239000002026 chloroform extract Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000003776 cleavage reaction Methods 0.000 description 10
- 230000007017 scission Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 9
- 239000012346 acetyl chloride Substances 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000001103 potassium chloride Substances 0.000 description 9
- 235000011164 potassium chloride Nutrition 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000007868 Raney catalyst Substances 0.000 description 7
- 229910000564 Raney nickel Inorganic materials 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 238000012512 characterization method Methods 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 6
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 6
- 229910003446 platinum oxide Inorganic materials 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- JIQXKYSNGXUDJU-UHFFFAOYSA-N propan-2-ylidenehydrazine Chemical compound CC(C)=NN JIQXKYSNGXUDJU-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- RHXARBUTTQDWBQ-UHFFFAOYSA-N C(C)N(C(CCl)CC(C)C)CC Chemical compound C(C)N(C(CCl)CC(C)C)CC RHXARBUTTQDWBQ-UHFFFAOYSA-N 0.000 description 3
- BQZQMSVYQMFIBC-UHFFFAOYSA-N CN(C)CC(C)=NNC(C)=O Chemical compound CN(C)CC(C)=NNC(C)=O BQZQMSVYQMFIBC-UHFFFAOYSA-N 0.000 description 3
- DGOIOPLWJLXHME-UHFFFAOYSA-N N'-[2-(dimethylamino)propan-2-yl]acetohydrazide Chemical compound CN(C)C(C)(C)NNC(C)=O DGOIOPLWJLXHME-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- YFGPJYNCAPSRRF-UHFFFAOYSA-N n'-(2-cyanoethyl)acetohydrazide Chemical compound CC(=O)NNCCC#N YFGPJYNCAPSRRF-UHFFFAOYSA-N 0.000 description 3
- CPDKIADBQMNDKM-UHFFFAOYSA-N n'-(2-cyanoethyl)benzohydrazide Chemical compound N#CCCNNC(=O)C1=CC=CC=C1 CPDKIADBQMNDKM-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229940117953 phenylisothiocyanate Drugs 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- VFPKIWATTACVJR-UHFFFAOYSA-N 1-(dimethylamino)propan-2-one Chemical compound CN(C)CC(C)=O VFPKIWATTACVJR-UHFFFAOYSA-N 0.000 description 2
- FDWXQMCNPYGCKA-UHFFFAOYSA-N 2-N',2-N'-diethyl-2-N-(propan-2-ylideneamino)propane-2,2-diamine Chemical compound C(C)N(CC)C(C)(C)NN=C(C)C FDWXQMCNPYGCKA-UHFFFAOYSA-N 0.000 description 2
- PUNDBTKEOORSOO-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-2-amine Chemical compound CN(C)C(C)(C)Cl PUNDBTKEOORSOO-UHFFFAOYSA-N 0.000 description 2
- UWDZGOJKFGZPPU-UHFFFAOYSA-N 3-hydrazinylpropanenitrile hydrochloride Chemical compound Cl.C(#N)CCNN UWDZGOJKFGZPPU-UHFFFAOYSA-N 0.000 description 2
- WQVAMFRPCWXWSS-UHFFFAOYSA-N 4-(dimethylamino)butan-2-one Chemical compound CN(C)CCC(C)=O WQVAMFRPCWXWSS-UHFFFAOYSA-N 0.000 description 2
- JRSKFKZAKLAAMS-UHFFFAOYSA-N 4-[methyl(propan-2-yl)amino]butan-2-one Chemical compound CC(C)N(C)CCC(C)=O JRSKFKZAKLAAMS-UHFFFAOYSA-N 0.000 description 2
- LPAFRKFJVMGTCA-UHFFFAOYSA-N CN(C)C(C)(C)NN=C(C)C Chemical compound CN(C)C(C)(C)NN=C(C)C LPAFRKFJVMGTCA-UHFFFAOYSA-N 0.000 description 2
- BIPRGADMSTUMFS-UHFFFAOYSA-N CN(C)N(N)C(C)C Chemical compound CN(C)N(N)C(C)C BIPRGADMSTUMFS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XAGBHSQDRJCYHK-UHFFFAOYSA-N N'-[2-(diethylamino)propan-2-yl]acetohydrazide Chemical compound C(C)N(CC)C(C)(C)NNC(C)=O XAGBHSQDRJCYHK-UHFFFAOYSA-N 0.000 description 2
- GYQSOLKGKZOBFO-UHFFFAOYSA-N N-amino-N-(diethylamino)propan-2-amine Chemical compound C(C)N(CC)N(N)C(C)C GYQSOLKGKZOBFO-UHFFFAOYSA-N 0.000 description 2
- SIVDSRPELCTQDJ-UHFFFAOYSA-N NCCCNNC(C1=CC=CC=C1)=O Chemical compound NCCCNNC(C1=CC=CC=C1)=O SIVDSRPELCTQDJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- SXWFEPUNSRLDRJ-UHFFFAOYSA-N n'-(3-aminopropyl)acetohydrazide Chemical compound CC(=O)NNCCCN SXWFEPUNSRLDRJ-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 2
- 150000003218 pyrazolidines Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GDXMMBDEMOUTNS-UHFFFAOYSA-N 1-(diethylamino)propan-2-one Chemical compound CCN(CC)CC(C)=O GDXMMBDEMOUTNS-UHFFFAOYSA-N 0.000 description 1
- DKUCGOKEZSOFOZ-UHFFFAOYSA-N 1-(dimethylamino)butan-2-one Chemical compound CCC(=O)CN(C)C DKUCGOKEZSOFOZ-UHFFFAOYSA-N 0.000 description 1
- QFWKNALJLPFSJH-UHFFFAOYSA-N 1-aminoazetidine-2,4-dione Chemical class NN1C(=O)CC1=O QFWKNALJLPFSJH-UHFFFAOYSA-N 0.000 description 1
- 208000010543 22q11.2 deletion syndrome Diseases 0.000 description 1
- FWIDNVRMQVAZDE-UHFFFAOYSA-N 3-(2-propan-2-ylidenehydrazinyl)propanenitrile Chemical compound CC(C)=NNCCC#N FWIDNVRMQVAZDE-UHFFFAOYSA-N 0.000 description 1
- ZYNIJUDUUIAGMQ-UHFFFAOYSA-N 3-hydrazinylpropan-1-amine Chemical compound NCCCNN ZYNIJUDUUIAGMQ-UHFFFAOYSA-N 0.000 description 1
- XLEOCTUCGZANAC-UHFFFAOYSA-N 4-(diethylamino)butan-2-one Chemical compound CCN(CC)CCC(C)=O XLEOCTUCGZANAC-UHFFFAOYSA-N 0.000 description 1
- HCRLXYVAWDRFBV-UHFFFAOYSA-N 5-(dimethylamino)pentan-2-one Chemical compound CN(C)CCCC(C)=O HCRLXYVAWDRFBV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LWUUNFWTPSERNA-UHFFFAOYSA-N CC(CN(C)C)=NNC(C1=CC=CC=C1)=O Chemical compound CC(CN(C)C)=NNC(C1=CC=CC=C1)=O LWUUNFWTPSERNA-UHFFFAOYSA-N 0.000 description 1
- APVIJHBLVPRQGS-UHFFFAOYSA-N CN(C)C(C)(C)NNC(C1=CC=CC=C1)=O Chemical compound CN(C)C(C)(C)NNC(C1=CC=CC=C1)=O APVIJHBLVPRQGS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- XVFFKVCNYWQBON-UHFFFAOYSA-N N-[1-(diethylamino)propan-2-ylideneamino]acetamide Chemical compound C(C)N(CC)CC(C)=NNC(C)=O XVFFKVCNYWQBON-UHFFFAOYSA-N 0.000 description 1
- LHGRNOJZWIASCS-UHFFFAOYSA-N N-[2-(diethylamino)propan-2-yl]acetohydrazide Chemical compound C(C)N(C(C)(C)N(N)C(C)=O)CC LHGRNOJZWIASCS-UHFFFAOYSA-N 0.000 description 1
- GJVNDTVCGIGRNN-UHFFFAOYSA-N N-[2-(dimethylamino)propan-2-yl]-N-(propan-2-ylideneamino)acetamide Chemical compound CN(C)C(C)(C)N(N=C(C)C)C(C)=O GJVNDTVCGIGRNN-UHFFFAOYSA-N 0.000 description 1
- VWIQPHZYQWTHGI-UHFFFAOYSA-N N-[2-(dimethylamino)propan-2-yl]acetohydrazide Chemical compound CN(C(C)(C)N(N)C(C)=O)C VWIQPHZYQWTHGI-UHFFFAOYSA-N 0.000 description 1
- YJRFYLQFBLJHNF-UHFFFAOYSA-N N1(CCCCC1)C(C)(C)NN Chemical compound N1(CCCCC1)C(C)(C)NN YJRFYLQFBLJHNF-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- JDXKTOBMLZLCSB-UHFFFAOYSA-N anilinothiourea Chemical compound NC(=S)NNC1=CC=CC=C1 JDXKTOBMLZLCSB-UHFFFAOYSA-N 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical class C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GJFBKLLFRJJEQX-UHFFFAOYSA-N n-methylpropan-2-amine;hydrochloride Chemical compound Cl.CNC(C)C GJFBKLLFRJJEQX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04Q—SELECTING
- H04Q11/00—Selecting arrangements for multiplex systems
- H04Q11/04—Selecting arrangements for multiplex systems for time-division multiplexing
- H04Q11/0407—Selecting arrangements for multiplex systems for time-division multiplexing using a stored programme control
Landscapes
- Engineering & Computer Science (AREA)
- Computer Networks & Wireless Communication (AREA)
- Time-Division Multiplex Systems (AREA)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Data Exchanges In Wide-Area Networks (AREA)
- Exchange Systems With Centralized Control (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE01446/72A SE353996B (cg-RX-API-DMAC7.html) | 1972-02-08 | 1972-02-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132666B true NO132666B (cg-RX-API-DMAC7.html) | 1975-09-01 |
| NO132666C NO132666C (cg-RX-API-DMAC7.html) | 1975-12-10 |
Family
ID=20258204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO498/73A NO132666C (cg-RX-API-DMAC7.html) | 1972-02-08 | 1973-02-07 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3818142A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS4889614A (cg-RX-API-DMAC7.html) |
| AU (1) | AU473237B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE795167A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1001274A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2306301C3 (cg-RX-API-DMAC7.html) |
| DK (1) | DK142069B (cg-RX-API-DMAC7.html) |
| FI (1) | FI57863C (cg-RX-API-DMAC7.html) |
| FR (1) | FR2171246B1 (cg-RX-API-DMAC7.html) |
| IT (1) | IT978930B (cg-RX-API-DMAC7.html) |
| NL (1) | NL7301527A (cg-RX-API-DMAC7.html) |
| NO (1) | NO132666C (cg-RX-API-DMAC7.html) |
| SE (1) | SE353996B (cg-RX-API-DMAC7.html) |
| SU (1) | SU659112A3 (cg-RX-API-DMAC7.html) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2246145B1 (cg-RX-API-DMAC7.html) * | 1973-07-20 | 1976-09-17 | Ibm France | |
| US3903370A (en) * | 1973-12-21 | 1975-09-02 | Bell Telephone Labor Inc | Line switch controller for a time division switching system |
| US4005272A (en) * | 1974-08-14 | 1977-01-25 | Arthur A. Collins, Inc. | Time folded TST (time space time) switch |
| US3975712A (en) * | 1975-02-18 | 1976-08-17 | Motorola, Inc. | Asynchronous communication interface adaptor |
| US4001781A (en) * | 1975-02-18 | 1977-01-04 | International Standard Electric Corporation | Electronic switching element |
| DE2618922C2 (de) * | 1976-04-29 | 1978-04-06 | Siemens Ag, 1000 Berlin Und 8000 Muenchen | Schaltungsanordnung für PCM-Zeitmultiplexvermittlungen |
| SE424498B (sv) * | 1977-09-09 | 1982-07-19 | Ellemtel Utvecklings Ab | Digitalt veljarenet |
| DE3122230A1 (de) * | 1981-06-04 | 1982-12-23 | Siemens AG, 1000 Berlin und 8000 München | Schaltungsanordnung fuer zeitmultiplex-fernmeldevermittlungsanlagen, insbesondere pcm-fernsprechvermittlungsanlagen, mit zeitmultiplexleitungen, deren zeitkanaele teils fuer nachrichtenverbindungen und teils zur uebertragung von signalisierungsinformationen dienen |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3458658A (en) * | 1965-09-14 | 1969-07-29 | New North Electric Co | Nonblocking switching system with reduced number of contacts |
| US3458659A (en) * | 1965-09-15 | 1969-07-29 | New North Electric Co | Nonblocking pulse code modulation system having storage and gating means with common control |
| US3585306A (en) * | 1968-05-16 | 1971-06-15 | Bell Telephone Labor Inc | Tandem office time division switching system |
| FR2032113A5 (cg-RX-API-DMAC7.html) * | 1969-02-19 | 1970-11-20 | Labo Cent Telecommunicat | |
| DE2108745C2 (de) * | 1971-02-24 | 1980-12-18 | Siemens Ag, 1000 Berlin Und 8000 Muenchen | Schaltungsanordnung zum Abschluß von Vierdrahtverbindungsleitungen mit nach dem Zeitmultiplexprinzip mit Pulscodemodulation gebildeten Nachrichtenkanälen an Vermittlungsstellen mit speicherprogrammierten Zentralsteuerwerken für Fernmelde-, insbesondere Fernsprechanlagen |
| US3694580A (en) * | 1971-07-28 | 1972-09-26 | Bell Telephone Labor Inc | Time division switching system |
| BE789402A (fr) * | 1971-10-01 | 1973-01-15 | Western Electric Co | Systeme de commutation a repartition temporelle |
-
0
- BE BE795167D patent/BE795167A/xx not_active IP Right Cessation
-
1972
- 1972-02-08 SE SE01446/72A patent/SE353996B/xx unknown
-
1973
- 1973-01-26 FI FI218/73A patent/FI57863C/sv active
- 1973-01-29 US US00327493A patent/US3818142A/en not_active Expired - Lifetime
- 1973-02-02 NL NL7301527A patent/NL7301527A/xx not_active Application Discontinuation
- 1973-02-05 AU AU51791/73A patent/AU473237B2/en not_active Expired
- 1973-02-07 NO NO498/73A patent/NO132666C/no unknown
- 1973-02-07 FR FR7304305A patent/FR2171246B1/fr not_active Expired
- 1973-02-07 DK DK66673AA patent/DK142069B/da not_active IP Right Cessation
- 1973-02-08 DE DE2306301A patent/DE2306301C3/de not_active Expired
- 1973-02-08 JP JP48015263A patent/JPS4889614A/ja active Pending
- 1973-02-08 IT IT20177/73A patent/IT978930B/it active
- 1973-02-08 CA CA163,254A patent/CA1001274A/en not_active Expired
- 1973-02-08 SU SU731881146A patent/SU659112A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4889614A (cg-RX-API-DMAC7.html) | 1973-11-22 |
| AU473237B2 (en) | 1976-06-17 |
| AU5179173A (en) | 1974-08-08 |
| DE2306301A1 (de) | 1973-08-23 |
| DK142069B (da) | 1980-08-18 |
| DK142069C (cg-RX-API-DMAC7.html) | 1981-02-09 |
| DE2306301B2 (de) | 1975-04-24 |
| IT978930B (it) | 1974-09-20 |
| FI57863C (fi) | 1980-10-10 |
| US3818142A (en) | 1974-06-18 |
| SU659112A3 (ru) | 1979-04-25 |
| DE2306301C3 (de) | 1975-12-04 |
| FR2171246B1 (cg-RX-API-DMAC7.html) | 1977-02-04 |
| FI57863B (fi) | 1980-06-30 |
| CA1001274A (en) | 1976-12-07 |
| SE353996B (cg-RX-API-DMAC7.html) | 1973-02-19 |
| FR2171246A1 (cg-RX-API-DMAC7.html) | 1973-09-21 |
| NL7301527A (cg-RX-API-DMAC7.html) | 1973-08-10 |
| NO132666C (cg-RX-API-DMAC7.html) | 1975-12-10 |
| BE795167A (fr) | 1973-05-29 |
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