NO136043B - - Google Patents
Download PDFInfo
- Publication number
- NO136043B NO136043B NO342471A NO342471A NO136043B NO 136043 B NO136043 B NO 136043B NO 342471 A NO342471 A NO 342471A NO 342471 A NO342471 A NO 342471A NO 136043 B NO136043 B NO 136043B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- starting material
- mercury
- production
- sulfur
- Prior art date
Links
- 239000007858 starting material Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003939 benzylamines Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 10
- -1 perfluoro compound Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 150000008359 benzonitriles Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RPKKPCOMUWMJOT-UHFFFAOYSA-N 1-fluoro-2-(2-phenylethyl)benzene Chemical group FC1=CC=CC=C1CCC1=CC=CC=C1 RPKKPCOMUWMJOT-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- AFMPMSCZPVNPEM-UHFFFAOYSA-N 2-bromobenzonitrile Chemical class BrC1=CC=CC=C1C#N AFMPMSCZPVNPEM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO342471A NO136043C (no) | 1971-01-22 | 1971-09-15 | Utgangsmateriale for anvendelse ved fremstilling av terapeutisk aktive benzylaminer. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO23471A NO130230B (en)) | 1971-01-22 | 1971-01-22 | |
| NO342471A NO136043C (no) | 1971-01-22 | 1971-09-15 | Utgangsmateriale for anvendelse ved fremstilling av terapeutisk aktive benzylaminer. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136043B true NO136043B (en)) | 1977-04-04 |
| NO136043C NO136043C (no) | 1977-07-13 |
Family
ID=19877460
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO23471A NO130230B (en)) | 1971-01-22 | 1971-01-22 | |
| NO342771A NO131832C (en)) | 1971-01-22 | 1971-09-15 | |
| NO342471A NO136043C (no) | 1971-01-22 | 1971-09-15 | Utgangsmateriale for anvendelse ved fremstilling av terapeutisk aktive benzylaminer. |
| NO342671A NO131724C (en)) | 1971-01-22 | 1971-09-15 | |
| NO342571A NO131831C (en)) | 1971-01-22 | 1971-09-15 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO23471A NO130230B (en)) | 1971-01-22 | 1971-01-22 | |
| NO342771A NO131832C (en)) | 1971-01-22 | 1971-09-15 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO342671A NO131724C (en)) | 1971-01-22 | 1971-09-15 | |
| NO342571A NO131831C (en)) | 1971-01-22 | 1971-09-15 |
Country Status (1)
| Country | Link |
|---|---|
| NO (5) | NO130230B (en)) |
-
1971
- 1971-01-22 NO NO23471A patent/NO130230B/no unknown
- 1971-09-15 NO NO342771A patent/NO131832C/no unknown
- 1971-09-15 NO NO342471A patent/NO136043C/no unknown
- 1971-09-15 NO NO342671A patent/NO131724C/no unknown
- 1971-09-15 NO NO342571A patent/NO131831C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO131724B (en)) | 1975-04-07 |
| NO131832C (en)) | 1975-08-20 |
| NO130230B (en)) | 1974-07-29 |
| NO131831B (en)) | 1975-05-05 |
| NO131831C (en)) | 1975-08-20 |
| NO131832B (en)) | 1975-05-05 |
| NO136043C (no) | 1977-07-13 |
| NO131724C (en)) | 1975-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| LU88049A1 (fr) | Bis(acyloxy-o)borate de l'(acide-o3,o4-6,7-substitue-8-alcoxy-l-cyclopropyl-1,4-dihydro-4-oxo-3-quinoleinecarboxylique et le sel de ce dernier,ainsi que leur procede de preparation | |
| CN105949147B (zh) | 一种绿色合成2-巯基苯并噻唑类衍生物的方法 | |
| US4127575A (en) | Preparation of chloro substituted pyridines | |
| US4093654A (en) | Production of pyridoxine intermediates from diketene | |
| CN111566075A (zh) | 一种制备克瑞沙硼的方法 | |
| EP0086678B1 (fr) | Procédé pour la préparation d'acyl-2 hexahydro-1,3,4,6,7,11b-2H-pyrazino (2,1-a)isoquinoléinones-4 et intermédiaires | |
| NO136043B (en)) | ||
| US20060142595A1 (en) | Process for preparing 5,6-dihydro-4-(S)-(ethylamino)-6-(S) methyl-4H-thieno[2,3b]thiopyran-2-sulphonamide-7,7-dioxide HCI | |
| US3101345A (en) | 2-hydroxymethyl-8-hydroxy-1,4-benzodioxane | |
| DE69230730T2 (de) | VERFAHREN ZUR HERSTELLUNG VON BENZO[b]NAPHTHYRIDINEN | |
| US2526232A (en) | Substituted hydantoins and methods for obtaining the same | |
| RU2722316C2 (ru) | Новый способ получения терифлуномида | |
| EP0204352B1 (de) | Verfahren zur Chlorierung von Alkylseitenketten stickstoffhaltiger Heterocyclen | |
| US5130434A (en) | Preparation of 3-methylquinoline-8-carboxylic acid | |
| US3574214A (en) | Hypochlorite process for chlorouracils | |
| JPS63267753A (ja) | α−（１−メチルエチル）−３，４−ジメトキシベンゼンアセトニトリルの製造方法、およびそれに使用される中間体化合物 | |
| JPS6116252B2 (en)) | ||
| KR840001039B1 (ko) | 벤조일 우레아의 제조방법 | |
| US4503238A (en) | Preparation of dihydro-4,4-dimethylfuran-2,3-dione | |
| US3371123A (en) | Process for preparing cf3cf2chrcl | |
| JPS59176234A (ja) | ｐ‐ニトロフエニル３−ブロモ−２，２−ジエトキシ−プロピオネート | |
| JPS6125713B2 (en)) | ||
| JPS5849556B2 (ja) | ３− ヒドロキシフタライドユウドウタイノセイホウ | |
| CN106220633A (zh) | 一种含氯苯并吡嗪结构的1,2,4‑三唑衍生物作为杀菌剂的应用 | |
| SU169503A1 (ru) | Способ получения 2,4-динитростирола |