NO117866B - - Google Patents
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- Publication number
- NO117866B NO117866B NO163322A NO16332266A NO117866B NO 117866 B NO117866 B NO 117866B NO 163322 A NO163322 A NO 163322A NO 16332266 A NO16332266 A NO 16332266A NO 117866 B NO117866 B NO 117866B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- react
- ester
- allowed
- monocarboxylic acid
- Prior art date
Links
- -1 aniline magnesium halide Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000003931 anilides Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 claims description 3
- VUHKTERBGMWQAY-UHFFFAOYSA-N N-(2-ethylphenyl)-1-propan-2-ylpiperidine-3-carboxamide Chemical compound C(C)C1=C(NC(C2CN(CCC2)C(C)C)=O)C=CC=C1 VUHKTERBGMWQAY-UHFFFAOYSA-N 0.000 claims description 2
- BOYAEDAIOHNLKU-UHFFFAOYSA-L [Br-].[Mg+2].ClC1=C(N)C(=CC=C1)C.[Br-] Chemical compound [Br-].[Mg+2].ClC1=C(N)C(=CC=C1)C.[Br-] BOYAEDAIOHNLKU-UHFFFAOYSA-L 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
- ZICBNHLULHJETL-UHFFFAOYSA-N ethyl 1-methylpiperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C ZICBNHLULHJETL-UHFFFAOYSA-N 0.000 claims description 2
- MCRPKBUFXAKDKI-UHFFFAOYSA-N ethyl pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1 MCRPKBUFXAKDKI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- ONXRNTKLIOTLCJ-UHFFFAOYSA-L magnesium 2,6-dimethylaniline dibromide Chemical compound [Br-].[Mg+2].CC1=C(N)C(=CC=C1)C.[Br-] ONXRNTKLIOTLCJ-UHFFFAOYSA-L 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- XIWBSOUNZWSFKU-UHFFFAOYSA-N ethyl piperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCNC1 XIWBSOUNZWSFKU-UHFFFAOYSA-N 0.000 claims 2
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims 1
- TWTWFMUQSOFTRN-UHFFFAOYSA-M CC[Mg]Br Chemical compound CC[Mg]Br TWTWFMUQSOFTRN-UHFFFAOYSA-M 0.000 claims 1
- HDHAIRSXHRAPHN-UHFFFAOYSA-L [Br-].[Mg+2].NC1=CC=CC=C1.[Br-] Chemical compound [Br-].[Mg+2].NC1=CC=CC=C1.[Br-] HDHAIRSXHRAPHN-UHFFFAOYSA-L 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- FCTZHFATVFONMW-UHFFFAOYSA-N n-phenylpyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC1=CC=CC=C1 FCTZHFATVFONMW-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- XQMUEFDDYYIRPT-UHFFFAOYSA-L [Br-].[Mg+2].C(C)C1=C(N)C=CC=C1.[Br-] Chemical compound [Br-].[Mg+2].C(C)C1=C(N)C=CC=C1.[Br-] XQMUEFDDYYIRPT-UHFFFAOYSA-L 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002681 magnesium compounds Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- DNZSDACGXYHMOL-UHFFFAOYSA-N n-(2-ethylphenyl)piperidine-3-carboxamide Chemical compound CCC1=CC=CC=C1NC(=O)C1CNCCC1 DNZSDACGXYHMOL-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J29/00—Details of cathode-ray tubes or of electron-beam tubes of the types covered by group H01J31/00
- H01J29/86—Vessels; Containers; Vacuum locks
- H01J29/867—Means associated with the outside of the vessel for shielding, e.g. magnetic shields
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J29/00—Details of cathode-ray tubes or of electron-beam tubes of the types covered by group H01J31/00
- H01J29/86—Vessels; Containers; Vacuum locks
- H01J29/87—Arrangements for preventing or limiting effects of implosion of vessels or containers
Landscapes
- Vessels, Lead-In Wires, Accessory Apparatuses For Cathode-Ray Tubes (AREA)
- Image-Pickup Tubes, Image-Amplification Tubes, And Storage Tubes (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6507304A NL6507304A (da) | 1965-06-09 | 1965-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117866B true NO117866B (da) | 1969-10-06 |
Family
ID=19793333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO163322A NO117866B (da) | 1965-06-09 | 1966-06-06 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3422220A (da) |
| AT (1) | AT259643B (da) |
| BE (1) | BE682209A (da) |
| CH (1) | CH446433A (da) |
| DE (1) | DE1462832A1 (da) |
| DK (1) | DK117724B (da) |
| ES (1) | ES327638A1 (da) |
| GB (1) | GB1146078A (da) |
| NL (1) | NL6507304A (da) |
| NO (1) | NO117866B (da) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1175444A (en) * | 1967-03-03 | 1969-12-23 | Thorn Aei Radio Valves & Tubes | Improvements in Implosion-Resistant Cathode Ray Tubes |
| US3541251A (en) * | 1967-09-19 | 1970-11-17 | Standard Elektrik Lorenz Ag | Implosion-protecting frame for television picture tubes and process for its installation |
| US3614519A (en) * | 1967-12-18 | 1971-10-19 | Zenith Radio Corp | Cathode-ray tube magnetic shield |
| JPS597731Y2 (ja) * | 1979-06-07 | 1984-03-09 | ソニー株式会社 | 陰極線管装置 |
| JPS5743347A (en) * | 1980-08-26 | 1982-03-11 | Mitsubishi Electric Corp | Cathode ray tube |
| GB2105956B (en) * | 1981-08-04 | 1985-02-06 | Tokyo Shibaura Electric Co | Cathode ray tube device |
| JPS5851683A (ja) * | 1981-09-22 | 1983-03-26 | Mitsubishi Electric Corp | 陰極線管装置の製造方法 |
| US4551765A (en) * | 1981-10-26 | 1985-11-05 | Allied Corporation | Cathode ray tube vibration isolator |
| US4556821A (en) * | 1984-03-15 | 1985-12-03 | Rca Corporation | Color image display system having an improved external magnetic shield |
| KR900001701B1 (ko) * | 1985-03-20 | 1990-03-19 | 미쯔비시 뎅기 가부시끼가이샤 | 칼라음극선관 |
| GB2177539B (en) * | 1985-05-20 | 1989-07-05 | Mitsubishi Electric Corp | Magnetic shielding system in color television receiver |
| IT1243083B (it) * | 1990-09-28 | 1994-05-23 | Videocolor Spa | Tubo a raggi catodici dotato di una fascia anti-implosione |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE627679A (da) * | 1962-01-29 | |||
| NL291096A (da) * | 1963-04-03 | |||
| US3369074A (en) * | 1965-04-02 | 1968-02-13 | Warwick Electronics Inc | Television tube shield and mounting structure |
-
1965
- 1965-06-09 NL NL6507304A patent/NL6507304A/xx unknown
-
1966
- 1966-05-10 US US549036A patent/US3422220A/en not_active Expired - Lifetime
- 1966-06-04 DE DE19661462832 patent/DE1462832A1/de active Pending
- 1966-06-06 CH CH813866A patent/CH446433A/de unknown
- 1966-06-06 GB GB25016/66A patent/GB1146078A/en not_active Expired
- 1966-06-06 DK DK290066AA patent/DK117724B/da unknown
- 1966-06-06 AT AT534766A patent/AT259643B/de active
- 1966-06-06 NO NO163322A patent/NO117866B/no unknown
- 1966-06-07 ES ES0327638A patent/ES327638A1/es not_active Expired
- 1966-06-07 BE BE682209D patent/BE682209A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK117724B (da) | 1970-05-25 |
| CH446433A (de) | 1967-11-15 |
| GB1146078A (en) | 1969-03-19 |
| ES327638A1 (es) | 1967-08-16 |
| DE1462832A1 (de) | 1968-12-05 |
| NL6507304A (da) | 1966-12-12 |
| AT259643B (de) | 1968-01-25 |
| BE682209A (da) | 1966-12-07 |
| US3422220A (en) | 1969-01-14 |
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