IL32434A - Process for the production of octahydro-1,2,4-metheno-pentalenyl-(5)-exo-isocyanate - Google Patents
Process for the production of octahydro-1,2,4-metheno-pentalenyl-(5)-exo-isocyanateInfo
- Publication number
- IL32434A IL32434A IL32434A IL3243469A IL32434A IL 32434 A IL32434 A IL 32434A IL 32434 A IL32434 A IL 32434A IL 3243469 A IL3243469 A IL 3243469A IL 32434 A IL32434 A IL 32434A
- Authority
- IL
- Israel
- Prior art keywords
- octahydro
- exo
- acid
- hydrazide
- carboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000012948 isocyanate Substances 0.000 title description 7
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims description 23
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- -1 alkoxyalkyl ester Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000001540 azides Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- XUAXJVSYRMEROP-UHFFFAOYSA-N C1C2=CC=3C(C(=CC13)C(=O)O)=C2 Chemical compound C1C2=CC=3C(C(=CC13)C(=O)O)=C2 XUAXJVSYRMEROP-UHFFFAOYSA-N 0.000 claims description 3
- LXAOOPAIGYABHJ-UHFFFAOYSA-N CCOCCOC(C1=CC(C2)=C3C1=CC2=C3)=O Chemical compound CCOCCOC(C1=CC(C2)=C3C1=CC2=C3)=O LXAOOPAIGYABHJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- KIAPWMKFHIKQOZ-UHFFFAOYSA-N 2-[[(4-fluorophenyl)-oxomethyl]amino]benzoic acid methyl ester Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(F)C=C1 KIAPWMKFHIKQOZ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- BTBORDOYETVCHQ-UHFFFAOYSA-N C(=O)=C1C(C(C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)=C=O)=C=O.[Ni] Chemical compound C(=O)=C1C(C(C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)=C=O)=C=O.[Ni] BTBORDOYETVCHQ-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH921368A CH498807A (de) | 1968-06-20 | 1968-06-20 | Verfahren zur Herstellung von Octahydro-1,2,4-methenopentalenyl-(5)-exo-isocyanat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32434A0 IL32434A0 (en) | 1969-08-27 |
| IL32434A true IL32434A (en) | 1973-03-30 |
Family
ID=4349576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32434A IL32434A (en) | 1968-06-20 | 1969-06-19 | Process for the production of octahydro-1,2,4-metheno-pentalenyl-(5)-exo-isocyanate |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT288347B (ro) |
| BE (1) | BE734866A (ro) |
| BG (1) | BG15558A3 (ro) |
| BR (1) | BR6909943D0 (ro) |
| CH (1) | CH498807A (ro) |
| CS (1) | CS154276B2 (ro) |
| DE (1) | DE1931181A1 (ro) |
| DK (1) | DK124025B (ro) |
| ES (1) | ES368537A1 (ro) |
| FR (1) | FR2011309A1 (ro) |
| GB (1) | GB1226446A (ro) |
| IL (1) | IL32434A (ro) |
| NL (1) | NL6909402A (ro) |
| PL (1) | PL72633B1 (ro) |
| RO (1) | RO56622A (ro) |
| SE (1) | SE358157B (ro) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0874244B1 (de) | 1997-04-19 | 2002-01-30 | LUST ANTRIEBSTECHNIK GmbH | Verfahren zum Messen von elektrischen Strömen in n Leitern sowie Vorrichtung zur Durchführung des Verfahrens |
-
1968
- 1968-06-20 CH CH921368A patent/CH498807A/de not_active IP Right Cessation
-
1969
- 1969-06-16 SE SE08529/69A patent/SE358157B/xx unknown
- 1969-06-16 DK DK323769AA patent/DK124025B/da unknown
- 1969-06-19 PL PL1969134276A patent/PL72633B1/pl unknown
- 1969-06-19 BG BG012484A patent/BG15558A3/bg unknown
- 1969-06-19 ES ES368537A patent/ES368537A1/es not_active Expired
- 1969-06-19 CS CS434469A patent/CS154276B2/cs unknown
- 1969-06-19 IL IL32434A patent/IL32434A/en unknown
- 1969-06-19 BE BE734866D patent/BE734866A/xx unknown
- 1969-06-19 RO RO60282A patent/RO56622A/ro unknown
- 1969-06-19 BR BR209943/69A patent/BR6909943D0/pt unknown
- 1969-06-19 NL NL6909402A patent/NL6909402A/xx unknown
- 1969-06-19 FR FR6920544A patent/FR2011309A1/fr not_active Withdrawn
- 1969-06-19 GB GB1226446D patent/GB1226446A/en not_active Expired
- 1969-06-19 AT AT585469A patent/AT288347B/de not_active IP Right Cessation
- 1969-06-19 DE DE19691931181 patent/DE1931181A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1226446A (ro) | 1971-03-31 |
| CS154276B2 (ro) | 1974-03-29 |
| FR2011309A1 (ro) | 1970-02-27 |
| DK124025B (da) | 1972-09-04 |
| BE734866A (ro) | 1969-12-19 |
| BG15558A3 (bg) | 1972-05-20 |
| AT288347B (de) | 1971-02-25 |
| PL72633B1 (ro) | 1974-08-30 |
| DE1931181A1 (de) | 1970-01-02 |
| IL32434A0 (en) | 1969-08-27 |
| RO56622A (ro) | 1974-04-29 |
| SE358157B (ro) | 1973-07-23 |
| ES368537A1 (es) | 1971-05-01 |
| BR6909943D0 (pt) | 1973-02-08 |
| NL6909402A (ro) | 1969-12-23 |
| CH498807A (de) | 1970-11-15 |
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