NO166026B - Anordning til forflytting av et utskiftbart lasteplan. - Google Patents
Anordning til forflytting av et utskiftbart lasteplan. Download PDFInfo
- Publication number
- NO166026B NO166026B NO873662A NO873662A NO166026B NO 166026 B NO166026 B NO 166026B NO 873662 A NO873662 A NO 873662A NO 873662 A NO873662 A NO 873662A NO 166026 B NO166026 B NO 166026B
- Authority
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- Norway
- Prior art keywords
- nitrite
- moving
- acid
- loading plan
- nitro
- Prior art date
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 claims description 4
- 150000003936 benzamides Chemical class 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- MODINVZWKNCELC-UHFFFAOYSA-N 4-chloro-2-methyl-5-nitrophenol Chemical compound CC1=CC(Cl)=C([N+]([O-])=O)C=C1O MODINVZWKNCELC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QIKYZXDTTPVVAC-UHFFFAOYSA-N 4-Aminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1 QIKYZXDTTPVVAC-UHFFFAOYSA-N 0.000 description 1
- WUSAYXHDBDAHGU-UHFFFAOYSA-N 4-chloro-2-methyl-5-nitroaniline Chemical compound CC1=CC(Cl)=C([N+]([O-])=O)C=C1N WUSAYXHDBDAHGU-UHFFFAOYSA-N 0.000 description 1
- QCSIFZMKKCWKBQ-UHFFFAOYSA-N 5-chloro-2-hydroxy-4-nitrobenzoic acid Chemical compound [N+](=O)([O-])C=1C=C(C(C(=O)O)=CC=1Cl)O QCSIFZMKKCWKBQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- -1 acetic acid Chemical class 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GJTDJAPHKDIQIQ-UHFFFAOYSA-L barium(2+);dinitrite Chemical compound [Ba+2].[O-]N=O.[O-]N=O GJTDJAPHKDIQIQ-UHFFFAOYSA-L 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- XNEQAVYOCNWYNZ-UHFFFAOYSA-L copper;dinitrite Chemical compound [Cu+2].[O-]N=O.[O-]N=O XNEQAVYOCNWYNZ-UHFFFAOYSA-L 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- AAJBNRZDTJPMTJ-UHFFFAOYSA-L magnesium;dinitrite Chemical compound [Mg+2].[O-]N=O.[O-]N=O AAJBNRZDTJPMTJ-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- ZVHHIDVFSYXCEW-UHFFFAOYSA-L nickel(ii) nitrite Chemical compound [Ni+2].[O-]N=O.[O-]N=O ZVHHIDVFSYXCEW-UHFFFAOYSA-L 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RAFRTSDUWORDLA-UHFFFAOYSA-N phenyl 3-chloropropanoate Chemical compound ClCCC(=O)OC1=CC=CC=C1 RAFRTSDUWORDLA-UHFFFAOYSA-N 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- Forklifts And Lifting Vehicles (AREA)
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- Vehicle Body Suspensions (AREA)
Description
Foreliggende oppfinnelse angår nye 3-nitro-4-halogen-fenolderivater som kan anvendes som utgangsmaterialer ved fremstilling av terapeutisk virksomme benzamider og som svarer til den generelle formel:
hvor R betegner en lavere alkoxycarbonylgruppe eller en lavere : . alkylgruppe og X betegner et. ha logen atom.
Disse nye forbindelser kan fremstilles ved at et 3-nit-ro-4-halogenairilinderivat med , den -generelle f ormel:
hvor R og X har de ovenfor angitte betydninger, omsettes med sal-petersyrling eller et metallnitrit i nærvær av en syre, og det erholdte diazoniumsalt behandles med vann.
Eksempler på anvendbare lavere alkoxycarbonylgruppér ér methoxycarbonyl, ethoxycarbonyl, butbxycarbonyl og isobutoxycar-bonyl. Eksempler på lavere alkylgruppér er methyl, ethyl, prbp-
yl, isppropyi, bu tyl og pen ty i.' "Eksempler på halogena tomer er klor og brom. "'" ' ' * : ~ ' • ' ■
Som den ovenfor nevnte syre anvendes fortrinnsvis en or-ganisk syre såsom eddiksyre, eller en vandig mineralsyre, såsom saltsyre, pérklorsyre eller svovelsyre, eller en vandig opplosning av natriumdihydfogenfosfat. Som eksempler på anvendbare me-tallnitriter kan nevnes natriumnitrit, kaliumnitrit, magnesiumni-trit, kalsiumnitrit, bariumnitrit, nikkelnitrit, kobbernitrit, kvikksolvnitrit og solvnitrit.
Spaltningen med vann av diazoniumsaltene som dannes i den ovenfor angitte reaksjon kan utfores uten at disse isoleres fra reaksjonsblandingen, og man får da den onskede forbindelse med den generelle formel (I). Alternativt kan diazoniumsaltene isoleres fra reaksjonsblandingen ved lav temperatur eller overfo-res til andre salter for man utforer spaltningen med vann for å danne de onskede forbindelser av formel (II). Det foretrekkes vanligvis å utfore spaltningen av diazoniumsaltet med vann under oppvarmning.
3-nitro-4-halogenfenolderivatene med den generelle formel (I) er som nevnt nyttige som utgangsmaterialer ved fremstilling av de tilsvarende benzamider, såsom N- (2-dialkylaminoaIkyl)-2-alkoxy-4-amino-5-halogenbenzamider. Disse benzamider har vik-tige terapeutiske egenskaper såsom analgetisk, antispasmodisk,
sedativ, anestetisk og antiemetisk virkning.
Således kan N-(diethylaminoethyl)-2-methoxy-4-amino-5-klorbenzamid, som er et kjent antiemetisk middel, fremstilles ut fra 2-methyl-4-klor-5-nitrofenol ved oxydasjon av denne forbindelse til 4-nitro-5-klorsalicylsyre, methylering av 2-hydroxy-gruppen med dimethylsulfat, forestring av syren, amidering av den erholdte ester med diethylaminoethylamin og påfolgende reduk-sjon av det herved dannede N-(diethylaminoethyl)-2-methoxy-4-nit-ro-5-klorbenzamid til det tilsvarende 4-aminobenzamid.
I nedenstående eksempel illustreres ytterligere hvordan de nye forbindelser med den generelle formel (I) kan fremstilles Eksempel
Til en avkjolt blanding av 40 ml konsentrert svovelsyre og 6 g natriumnitrit blev der under omrbring og under opprett-holdelse av en temperatur i blandingen under 20°C tilsatt dråpe-vis en opplbsning av 14,4 g 4-klor-5-nitro-orthotoluidin i 185 ml iseddik. Efter at hele denne opplosning var tilsatt, blev blandingen omrdrt i ytterligere en time, hvorefter den blev tilsatt fortynnet svovelsyre fremstillet ved blanding av 80 ml konsentrert svovelsyre og 60 ml vann. Reaksjonsblandingen blev der-på oppvarmet under omrbring i 1 time på oljebad med temperatur 150°C. Man JLot den derefter stå under fortsatt omroring. Efter henstand natten over blev reaksjonsblandingen heldt i isvann, hvorved der blev utskilt krystaller som blev oppsamlet ved fil-trering under sug. Krystallene blev vasket med isvann og derefter tbrret, hvorved man fikk 12,12 g uren 2-methyl-4-klor-5-nit-rofenol med smeltepunkt 142 - 144°C. Utbyttet var 83,5 %. Dette urene produkt blev omkrystallisert fra 50 %'s ethanol, hvorved man fikk et renset produkt i form av svakt gule nåler med smeltepunkt 142 - 144°C.
Analyse: Beregnet for C^H^OgNCl:
C 44,82; H 3,22; N 7,47; Cl 18,90.
Funnet: G 44,98; H 3,31; N 7,60; Cl 18,90.
Claims (1)
- 3-nitro-4-halogenfenolderivater for anvendelse som ut-gangsmateriale■ved fremstilling av de tilsvarende terapeutisk virksomme benzamider, karakterisert ved at de har den generelle formel:hvor R betegner en lavere alkoxycarbonylgruppe eller en lavere alkylgruppe, og X betegner et halogenatom.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO873662A NO166026B (no) | 1987-08-31 | 1987-08-31 | Anordning til forflytting av et utskiftbart lasteplan. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO873662A NO166026B (no) | 1987-08-31 | 1987-08-31 | Anordning til forflytting av et utskiftbart lasteplan. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO873662D0 NO873662D0 (no) | 1987-08-31 |
| NO873662L NO873662L (no) | 1989-03-02 |
| NO166026B true NO166026B (no) | 1991-02-11 |
Family
ID=19890196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO873662A NO166026B (no) | 1987-08-31 | 1987-08-31 | Anordning til forflytting av et utskiftbart lasteplan. |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO166026B (no) |
-
1987
- 1987-08-31 NO NO873662A patent/NO166026B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO873662L (no) | 1989-03-02 |
| NO873662D0 (no) | 1987-08-31 |
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