CH444182A - Verfahren zur Herstellung von organischen Phosphorverbindungen - Google Patents

Verfahren zur Herstellung von organischen Phosphorverbindungen

Info

Publication number: CH444182A
Authority: CH; Switzerland
Prior art keywords: formula; hydrogen; bis; reaction; carried out
Prior art date: 1960-12-09

Application number

CH465163A

Other languages

German (de)

English (en)

Inventor

Cooper Brown Norman

Thomas Hollinshead Donald

Original Assignee

Cooper Mcdougall & Robertson

Priority date (The priority date 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 date listed.)

1960-12-09

Filing date

1963-04-11

Publication date

1967-09-30

1960-12-09 Priority claimed from GB42557/60A external-priority patent/GB1007332A/en

1962-04-18 Priority claimed from GB15146/62A external-priority patent/GB1030621A/en

1963-04-11 Application filed by Cooper Mcdougall & Robertson filed Critical Cooper Mcdougall & Robertson

1967-09-30 Publication of CH444182A publication Critical patent/CH444182A/de

Links

238000000034 method Methods 0.000 title claims description 12
150000002903 organophosphorus compounds Chemical class 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title description 2
-1 alkyl radical Chemical class 0.000 claims description 18
229910052698 phosphorus Inorganic materials 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000011574 phosphorus Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
229910052751 metal Chemical group 0.000 claims 1
239000002184 metal Chemical group 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
229910019142 PO4 Inorganic materials 0.000 description 10
239000000203 mixture Substances 0.000 description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 10
239000010452 phosphate Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000002904 solvent Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000007787 solid Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
SNMUERBNQDOIQB-UHFFFAOYSA-N ethyl 7-hydroxy-2-oxochromene-4-carboxylate Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C(=O)OCC SNMUERBNQDOIQB-UHFFFAOYSA-N 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
238000003756 stirring Methods 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000244206 Nematoda Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000013078 crystal Substances 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
239000005457 ice water Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
241001147657 Ancylostoma Species 0.000 description 1
241000760148 Aspiculuris tetraptera Species 0.000 description 1
IDABAEPWKOIGNM-UHFFFAOYSA-N CC[Na].OC(=O)CC(=O)C(O)=O Chemical compound CC[Na].OC(=O)CC(=O)C(O)=O IDABAEPWKOIGNM-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000253350 Capillaria Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
241000243976 Haemonchus Species 0.000 description 1
241000243780 Heligmosomoides polygyrus Species 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241001137882 Nematodirus Species 0.000 description 1
241001494479 Pecora Species 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
241000244174 Strongyloides Species 0.000 description 1
241000975692 Syphacia obvelata Species 0.000 description 1
241000243797 Trichostrongylus Species 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
GGCXLVWDCPTFMN-UHFFFAOYSA-N bis(2-chloroethyl) hydrogen phosphite Chemical compound ClCCOP(O)OCCCl GGCXLVWDCPTFMN-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
SKLJNPYYJVTRBG-UHFFFAOYSA-N chloro-bis(2-chloroethyl)phosphane Chemical class ClCCP(CCCl)Cl SKLJNPYYJVTRBG-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000029087 digestion Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
UNIGUELVFGIULR-UHFFFAOYSA-N ethyl 2-(7-hydroxy-4-methyl-2-oxochromen-3-yl)acetate Chemical compound C1=C(O)C=C2OC(=O)C(CC(=O)OCC)=C(C)C2=C1 UNIGUELVFGIULR-UHFFFAOYSA-N 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229940072033 potash Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
- 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH465163A 1960-12-09 1963-04-11 Verfahren zur Herstellung von organischen Phosphorverbindungen CH444182A (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB42557/60A GB1007332A (en)	1960-12-09	1960-12-09	New halogen-containing phosphoric and thiophosphoric acid esters and formulations containing them
GB2553261		1961-07-14
GB15146/62A GB1030621A (en)	1962-04-18	1962-04-18	New halogen-containing phosphoric acid esters and compositions

Publications (1)

Publication Number	Publication Date
CH444182A true CH444182A (de)	1967-09-30

Family

ID=26200850

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH465163A CH444182A (de)	1960-12-09	1963-04-11	Verfahren zur Herstellung von organischen Phosphorverbindungen

Country Status (3)

Country	Link
BE (1)	BE631255A (pt)
CH (1)	CH444182A (pt)
FR (1)	FR84110E (pt)

1963
- 1963-04-11 CH CH465163A patent/CH444182A/de unknown
- 1963-04-18 BE BE631255A patent/BE631255A/xx unknown
- 1963-04-18 FR FR931875A patent/FR84110E/fr not_active Expired

Also Published As

Publication number	Publication date
FR84110E (fr)	1964-11-27
BE631255A (pt)	1963-11-18

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