DE1099532B - Verfahren zur Herstellung von Thionophosphonsaeureamidfluoriden - Google Patents
Verfahren zur Herstellung von ThionophosphonsaeureamidfluoridenInfo
- Publication number
- DE1099532B DE1099532B DEF27844A DEF0027844A DE1099532B DE 1099532 B DE1099532 B DE 1099532B DE F27844 A DEF27844 A DE F27844A DE F0027844 A DEF0027844 A DE F0027844A DE 1099532 B DE1099532 B DE 1099532B
- Authority
- DE
- Germany
- Prior art keywords
- solution
- benzene
- ecm
- fluoride
- thionophosphonic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 acid amide fluorides Chemical class 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 120
- 239000000203 mixture Substances 0.000 claims description 23
- 241000700159 Rattus Species 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 230000001988 toxicity Effects 0.000 claims description 4
- 231100000419 toxicity Toxicity 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 45
- 238000003756 stirring Methods 0.000 description 20
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 15
- 238000009835 boiling Methods 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- APNXZXPWHTUIQL-UHFFFAOYSA-N FP(F)=O Chemical compound FP(F)=O APNXZXPWHTUIQL-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 241001454295 Tetranychidae Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- WXJXBKBJAKPJRN-UHFFFAOYSA-N Methanephosphonothioic acid Chemical compound CP(O)(O)=S WXJXBKBJAKPJRN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RSXPIJKXIOZTFO-UHFFFAOYSA-N ethenyl-dihydroxy-sulfanylidene-lambda5-phosphane Chemical compound C(=C)P(O)(O)=S RSXPIJKXIOZTFO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- ILLKOMOQDNCTMI-UHFFFAOYSA-N ethyl-difluoro-sulfanylidene-$l^{5}-phosphane Chemical compound CCP(F)(F)=S ILLKOMOQDNCTMI-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- RRSMHQNLDRCPQG-UHFFFAOYSA-N methanamine;hydrofluoride Chemical compound [F-].[NH3+]C RRSMHQNLDRCPQG-UHFFFAOYSA-N 0.000 description 2
- LVKUAMRYYGCOLC-UHFFFAOYSA-N n-methylmethanamine;hydrofluoride Chemical compound [F-].C[NH2+]C LVKUAMRYYGCOLC-UHFFFAOYSA-N 0.000 description 2
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- AAMOGWIDQKYZIU-UHFFFAOYSA-N difluoro-methyl-sulfanylidene-$l^{5}-phosphane Chemical compound CP(F)(F)=S AAMOGWIDQKYZIU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HGELWZQRZUOEOJ-UHFFFAOYSA-N ethyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCP(O)(O)=S HGELWZQRZUOEOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/564—Three-membered rings
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
-
- 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL248976D NL248976A (en, 2012) | 1959-03-03 | ||
| NL129442D NL129442C (en, 2012) | 1959-03-03 | ||
| BE588254D BE588254A (en, 2012) | 1959-03-03 | ||
| DEF27844A DE1099532B (de) | 1959-03-03 | 1959-03-03 | Verfahren zur Herstellung von Thionophosphonsaeureamidfluoriden |
| CH191660A CH386411A (de) | 1959-03-03 | 1960-02-19 | Verfahren zur Herstellung von Thiono-phosphonsäure-fluoramiden |
| US11951A US3184465A (en) | 1959-03-03 | 1960-03-01 | Alkenyl thionophosphonic acid fluoramides |
| GB7619/60A GB883982A (en) | 1959-03-03 | 1960-03-03 | Thionophosphonic acid fluoramides |
| FR820318A FR1250923A (fr) | 1959-03-03 | 1960-03-03 | Procédé de préparation de fluoramides d'acides thionophosphoniques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF27844A DE1099532B (de) | 1959-03-03 | 1959-03-03 | Verfahren zur Herstellung von Thionophosphonsaeureamidfluoriden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1099532B true DE1099532B (de) | 1961-02-16 |
Family
ID=7092627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF27844A Pending DE1099532B (de) | 1959-03-03 | 1959-03-03 | Verfahren zur Herstellung von Thionophosphonsaeureamidfluoriden |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3184465A (en, 2012) |
| BE (1) | BE588254A (en, 2012) |
| CH (1) | CH386411A (en, 2012) |
| DE (1) | DE1099532B (en, 2012) |
| GB (1) | GB883982A (en, 2012) |
| NL (2) | NL129442C (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5441961A (en) * | 1992-08-27 | 1995-08-15 | Eli Lilly And Company | Substituted cyclo or bicycloalkylamides of (8β)-6-(substituted) ergolines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US729586A (en) * | 1901-07-09 | 1903-06-02 | Ernst Gustav Hoffmann | Road-vehicle. |
| BE550319A (en, 2012) * | 1953-11-13 |
-
0
- NL NL248976D patent/NL248976A/xx unknown
- BE BE588254D patent/BE588254A/xx unknown
- NL NL129442D patent/NL129442C/xx active
-
1959
- 1959-03-03 DE DEF27844A patent/DE1099532B/de active Pending
-
1960
- 1960-02-19 CH CH191660A patent/CH386411A/de unknown
- 1960-03-01 US US11951A patent/US3184465A/en not_active Expired - Lifetime
- 1960-03-03 GB GB7619/60A patent/GB883982A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL129442C (en, 2012) | 1900-01-01 |
| GB883982A (en) | 1961-12-06 |
| NL248976A (en, 2012) | 1900-01-01 |
| BE588254A (en, 2012) | 1900-01-01 |
| CH386411A (de) | 1965-01-15 |
| US3184465A (en) | 1965-05-18 |
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