IL25189A - Process for the preparation of 20 pyrazinyl phosphorothioates - Google Patents
Process for the preparation of 20 pyrazinyl phosphorothioatesInfo
- Publication number
- IL25189A IL25189A IL25189A IL2518966A IL25189A IL 25189 A IL25189 A IL 25189A IL 25189 A IL25189 A IL 25189A IL 2518966 A IL2518966 A IL 2518966A IL 25189 A IL25189 A IL 25189A
- Authority
- IL
- Israel
- Prior art keywords
- phosphorochloridothioate
- pyrazinyl
- alkali metal
- hydroxypyrazine
- preparing
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- KTXXEFQDZCVEQJ-UHFFFAOYSA-N dihydroxy-pyrazin-2-yloxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(=S)OC1=CN=CC=N1 KTXXEFQDZCVEQJ-UHFFFAOYSA-N 0.000 title claims description 3
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 claims description 13
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- -1 alkali metal salt Chemical class 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000000034 method Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PXEGUCRXJYLKLJ-UHFFFAOYSA-M sodium;pyrazin-2-olate Chemical compound [Na+].[O-]C1=CN=CC=N1 PXEGUCRXJYLKLJ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US438724A US3340262A (en) | 1965-03-10 | 1965-03-10 | Process for the preparation of o, o-dialkyl-o-2-pyrazinyl phosphorothioates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL25189A true IL25189A (en) | 1969-08-27 |
Family
ID=23741766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL25189A IL25189A (en) | 1965-03-10 | 1966-02-15 | Process for the preparation of 20 pyrazinyl phosphorothioates |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3340262A (da) |
| BE (1) | BE676636A (da) |
| BR (1) | BR6677712D0 (da) |
| CH (1) | CH469028A (da) |
| DE (1) | DE1645895C3 (da) |
| DK (1) | DK112170B (da) |
| GB (1) | GB1062386A (da) |
| IL (1) | IL25189A (da) |
| IT (1) | IT941498B (da) |
| NL (1) | NL6603006A (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3880997A (en) * | 1965-05-26 | 1975-04-29 | Bayer Ag | Insecticidal and acaricidal phosphorous-containing esters of 2-hydroxyquinoxaline |
| US3505328A (en) * | 1968-09-16 | 1970-04-07 | American Cyanamid Co | O,o-dimethyl-o-(5,6-dimethyl-2-pyrazinyl) phosphorothioate |
| US3539332A (en) * | 1968-12-23 | 1970-11-10 | Dow Chemical Co | Pyrazine compositions and method of use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE570965A (da) * | 1957-09-06 | 1900-01-01 | ||
| NL286455A (da) * | 1962-01-09 | 1900-01-01 |
-
1965
- 1965-03-10 US US438724A patent/US3340262A/en not_active Expired - Lifetime
-
1966
- 1966-02-15 IL IL25189A patent/IL25189A/en unknown
- 1966-02-17 IT IT3502/66A patent/IT941498B/it active
- 1966-02-17 BE BE676636D patent/BE676636A/xx not_active Expired
- 1966-02-18 GB GB7354/66A patent/GB1062386A/en not_active Expired
- 1966-03-03 DK DK111666AA patent/DK112170B/da unknown
- 1966-03-08 NL NL6603006A patent/NL6603006A/xx unknown
- 1966-03-08 DE DE1645895A patent/DE1645895C3/de not_active Expired
- 1966-03-09 BR BR177712/66A patent/BR6677712D0/pt unknown
- 1966-03-10 CH CH341666A patent/CH469028A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1645895A1 (de) | 1970-09-17 |
| BR6677712D0 (pt) | 1973-09-11 |
| DK112170B (da) | 1968-11-18 |
| NL6603006A (da) | 1966-09-12 |
| DE1645895C3 (de) | 1974-05-02 |
| CH469028A (de) | 1969-02-28 |
| GB1062386A (en) | 1967-03-22 |
| BE676636A (da) | 1966-08-17 |
| US3340262A (en) | 1967-09-05 |
| IT941498B (it) | 1973-03-01 |
| DE1645895B2 (de) | 1973-10-04 |
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