GB681102A - Aryl esters of acid phosphorus compounds - Google Patents
Aryl esters of acid phosphorus compoundsInfo
- Publication number
- GB681102A GB681102A GB2364/50A GB236450A GB681102A GB 681102 A GB681102 A GB 681102A GB 2364/50 A GB2364/50 A GB 2364/50A GB 236450 A GB236450 A GB 236450A GB 681102 A GB681102 A GB 681102A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethylaminophenyl
- benzene
- reacted
- phosphorus
- dimethylaminophenol
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 title abstract 5
- 150000007860 aryl ester derivatives Chemical class 0.000 title 1
- 150000003018 phosphorus compounds Chemical class 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 10
- -1 piperidinoalkyl Chemical group 0.000 abstract 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 abstract 7
- 229910052708 sodium Inorganic materials 0.000 abstract 7
- 239000011734 sodium Substances 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 6
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 abstract 5
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 abstract 4
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 abstract 4
- AUABZJZJXPSZCN-UHFFFAOYSA-N 2-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC=C1O AUABZJZJXPSZCN-UHFFFAOYSA-N 0.000 abstract 3
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- STCAMFQRWJVQKV-UHFFFAOYSA-N CN(C=1C=C(C=CC1)P(=O)(C1=CC(=CC=C1)N(C)C)Cl)C Chemical compound CN(C=1C=C(C=CC1)P(=O)(C1=CC(=CC=C1)N(C)C)Cl)C STCAMFQRWJVQKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 2
- FMBVPEVOEJNBQU-UHFFFAOYSA-N 4-[chloro-[4-(dimethylamino)phenyl]phosphinothioyl]-N,N-dimethylaniline Chemical compound CN(C1=CC=C(C=C1)P(=S)(C1=CC=C(C=C1)N(C)C)Cl)C FMBVPEVOEJNBQU-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 2
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 abstract 2
- 150000003017 phosphorus Chemical class 0.000 abstract 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- 239000000725 suspension Substances 0.000 abstract 2
- WFZSFSMELSBBJO-UHFFFAOYSA-N 1-(piperidin-1-ylmethyl)naphthalen-2-ol Chemical compound OC1=CC=C2C=CC=CC2=C1CN1CCCCC1 WFZSFSMELSBBJO-UHFFFAOYSA-N 0.000 abstract 1
- LYBPBRBKERCUNO-UHFFFAOYSA-N 2-(piperidin-1-ylmethyl)naphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2C(O)=C1CN1CCCCC1 LYBPBRBKERCUNO-UHFFFAOYSA-N 0.000 abstract 1
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 abstract 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenylpropanol Natural products OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 abstract 1
- JLVDKKXLBJRCMN-UHFFFAOYSA-N 3-[chloro-[3-(dimethylamino)phenyl]phosphinothioyl]-N,N-dimethylaniline Chemical compound CN(C=1C=C(C=CC1)P(=S)(C1=CC(=CC=C1)N(C)C)Cl)C JLVDKKXLBJRCMN-UHFFFAOYSA-N 0.000 abstract 1
- NOEWSUPPMSWBIF-UHFFFAOYSA-N 3-bis[3-(diethylamino)phenoxy]phosphinothioyloxy-N,N-diethylaniline Chemical compound P(=S)(OC1=CC(=CC=C1)N(CC)CC)(OC1=CC(=CC=C1)N(CC)CC)OC1=CC(=CC=C1)N(CC)CC NOEWSUPPMSWBIF-UHFFFAOYSA-N 0.000 abstract 1
- NFVPEIKDMMISQO-UHFFFAOYSA-N 4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C=C1 NFVPEIKDMMISQO-UHFFFAOYSA-N 0.000 abstract 1
- GWWHLTLNGLUFJX-UHFFFAOYSA-N 4-[2-dihydroxyphosphinothioyloxy-2-[4-(dimethylamino)phenyl]propyl]-N,N-dimethylaniline Chemical compound CC(CC1=CC=C(C=C1)N(C)C)(C2=CC=C(C=C2)N(C)C)OP(=S)(O)O GWWHLTLNGLUFJX-UHFFFAOYSA-N 0.000 abstract 1
- ISCNHWQSPWNEMX-UHFFFAOYSA-N 4-[3-(dimethylamino)butyl]phenol Chemical compound CN(C)C(C)CCC1=CC=C(O)C=C1 ISCNHWQSPWNEMX-UHFFFAOYSA-N 0.000 abstract 1
- QZNMJYSVCFULIX-UHFFFAOYSA-N 4-bis[4-(dimethylamino)phenoxy]phosphinothioyloxy-N,N-dimethylaniline Chemical compound P(=S)(OC1=CC=C(C=C1)N(C)C)(OC1=CC=C(C=C1)N(C)C)OC1=CC=C(C=C1)N(C)C QZNMJYSVCFULIX-UHFFFAOYSA-N 0.000 abstract 1
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- HHLOKWVXMOJLQY-UHFFFAOYSA-N C1(CCCCC1)P(O)(=O)O.CCCCCCC Chemical class C1(CCCCC1)P(O)(=O)O.CCCCCCC HHLOKWVXMOJLQY-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Chemical class 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Chemical class 0.000 abstract 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000004792 aryl magnesium halides Chemical class 0.000 abstract 1
- GWWWNAKRFFANNF-UHFFFAOYSA-N bis(dimethylamino)phosphinic acid Chemical compound CN(C)P(O)(=O)N(C)C GWWWNAKRFFANNF-UHFFFAOYSA-N 0.000 abstract 1
- FTEJLGWSZIUWSZ-UHFFFAOYSA-N chloro-n,n-dimethylphosphonamidic acid Chemical compound CN(C)P(O)(Cl)=O FTEJLGWSZIUWSZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000544 cholinesterase inhibitor Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 abstract 1
- SXIWNIQDOJKDGB-UHFFFAOYSA-N dichloro-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound ClP(Cl)(=S)C1=CC=CC=C1 SXIWNIQDOJKDGB-UHFFFAOYSA-N 0.000 abstract 1
- NAKDJXIEBCHXIZ-UHFFFAOYSA-N dihydroxy-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(=S)C1=CC=CC=C1 NAKDJXIEBCHXIZ-UHFFFAOYSA-N 0.000 abstract 1
- OUMFRZJDHOKSPJ-UHFFFAOYSA-N dimethylaminophosphonic acid Chemical compound CN(C)P(O)(O)=O OUMFRZJDHOKSPJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- YNNWHXDQGXCGIF-UHFFFAOYSA-N n-dihydroxyphosphinothioyl-n-methylmethanamine Chemical class CN(C)P(O)(O)=S YNNWHXDQGXCGIF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical compound FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 abstract 1
- 229940075930 picrate Drugs 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 235000013024 sodium fluoride Nutrition 0.000 abstract 1
- 239000011775 sodium fluoride Substances 0.000 abstract 1
- 239000001488 sodium phosphate Substances 0.000 abstract 1
- 229910000162 sodium phosphate Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- OWNZHTHZRZVKSQ-UHFFFAOYSA-N tribromo(sulfanylidene)-$l^{5}-phosphane Chemical compound BrP(Br)(Br)=S OWNZHTHZRZVKSQ-UHFFFAOYSA-N 0.000 abstract 1
- UWZXHPKHQVFFRM-UHFFFAOYSA-N tris[3-(dimethylamino)phenyl] phosphate Chemical compound P(=O)(OC1=CC(=CC=C1)N(C)C)(OC1=CC(=CC=C1)N(C)C)OC1=CC(=CC=C1)N(C)C UWZXHPKHQVFFRM-UHFFFAOYSA-N 0.000 abstract 1
- WWIAHPNPGMPSAO-UHFFFAOYSA-N tris[3-(dimethylamino)phenyl] phosphite Chemical compound P(OC1=CC(=CC=C1)N(C)C)(OC1=CC(=CC=C1)N(C)C)OC1=CC(=CC=C1)N(C)C WWIAHPNPGMPSAO-UHFFFAOYSA-N 0.000 abstract 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 abstract 1
Classifications
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1406—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-aryl
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
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- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
-
- 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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
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- 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)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
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)
Abstract
The invention comprises basically substituted aryl esters of acid derivatives of phosphorus, of the general formula <FORM:0681102/IV (b)/1> (wherein Ar represents phenyl or naphthyl carrying as substituent at least one dialkylamino, dialkylaminoalkyl, piperidino, piperidinoalkyl, morpholino or morpholinoalkyl group, n is 1, 2 or 3, and X represents halogen, amino, substituted amino, hydroxy, substituted hydroxy, alkyl, cycloalkyl, aralkyl or aryl, X being absent when n is 3 and the two X's being identical or different when n is 1), and salts of such esters, and the manufacture thereof by reacting a basically substituted phenol or naphthol, ArOH, or an alkali metal derivative thereof, with a halide of an acid derivative of phosphorus, of the formula <FORM:0681102/IV (b)/2> (wherein Y represents halogen), advantageously in a relatively inert solvent or diluent, and, if desired, reacting the product, if it still contains halogen, with ammonia or a primary or secondary amine, or with an alkali, or with ammonium or alkali metal fluoride, or with an alkyl or aryl magnesium halide. When the free phenol or naphthol is used, the product is obtained in the form of a hydrohalide unless, as is preferred, the reaction is carried out in the presence of an acid acceptor (advantageously a tertiary amine). The products have therapeutic utility as cholinesterase inhibitors. In examples: (1) phosphorus oxychloride is reacted with 3 molecular proportions of m-dimethylaminophenol in benzene in the presence of triethylamine or pyridine to produce tri-(m-dimethylaminophenyl) phosphate, which may be converted into its methiodide, picrate, methomethyl sulphate, hydrochloride, sulphate, perchlorate and oxalate; (2) phosphorus oxychloride is reacted with 3 molecular proportions of m-diethylaminophenol in aqueous caustic soda; (3) phosphorus oxychloride is reacted with o-dimethylaminophenol as in (1), or with a benzene suspension of sodium o-dimethylaminophenate; (4)-(9) the o-dimethylaminophenol in (3) is replaced by p-dimethylamino-or o- or p-dimethylaminomethyl-phenol, 1-dimethylaminomethyl- or 1-piperidinomethyl-2-naphthol, or 2-piperidinomethyl-1-naphthol; (10) phosphorus trichloride is reacted with 3 molecular proportions of m-dimethylaminophenol is benzene in the presence of triethylamine, or with a suspension of sodium m-dimethylaminophenate in ether, producing tri-(m-dimethylaminophenyl) phosphite; (11) the m-dimethylaminophenol in (10) is replaced by the p-isomer; (12) phosphorus thiochloride is reacted with 2 molecular proportions of p-dimethylaminophenol in benzene in the presence of triethylamine to form di-(p-dimethylaminophenyl)-thiophosphoryl chloride; (13) the p-dimethylaminophenol in (12) is replaced by the m-isomer; (14) the phosphorus thiochloride in (13) is replaced by the oxychloride, and the resulting di - (m - dimethylaminophenyl) - phosphoryl chloride is reacted with ammonium fluoride to give the corresponding phosphoryl fluoride; (15) the product of (12) is treated with ammonium or sodium fluoride in isopropanol; (16) the product of (12) is reacted with sodium p-dimethylaminophenate in isopropanol to produce tri-(p-dimethylaminophenyl) thiophosphate; the same product is obtained by reacting phosphorus thiochloride with 3 molecular proportions of p-dimethylaminophenol in toluene in the presence of triethylamine and phosphorus trichloride; (17)-(20) the product of (12) is reacted with a solution of sodium in isopropanol, aqueous ammonia, aqueous methylamine or a solution of dimethylamine in benzene, producing respectively di - (p - dimethylaminophenyl) - isopropyl thiophosphate and the di-(p-dimethylaminophenyl) esters of amino-, methylamino-and dimethylamino-thiophosphonic acids; (21) the di-(m-dimethylaminophenyl) ester of dimethylaminophosphonic acid is prepared by reacting di - (m - dimethylaminophenyl) - phosphoryl chloride with excess dimethylamine in benzene, or by reacting dimethylaminophosphonyl chloride with 2 molecular proportions of sodium m-dimethylaminophenate, or of m-dimethylaminophenol in the presence of triethylamine; (22) dimethylaminophosphonyl chloride is reacted with an equimolecular proportion of m-dimethylaminophenol in benzene in the presence of triethylamine to yield the m - dimethylaminophenyl ester of chlorodimethylaminophosphinic acid; (23) the product of (22) is reacted with dimethylamine in benzene to produce the m-dimethylaminophenyl ester of di-(dimethylamino)-phosphinic acid; (24) the phosphorus thiochloride in (12) is replaced by phosphorus thiobromide; (25) di-(m-dimethylaminophenyl)-thiophosphoryl chloride and sodium m-dimethylaminophenate are reacted as in (16); (26) and (27) the o-dimethylaminophenol in (3) is replaced by p-dimethylaminocarvacrol or p-(3-dimethylaminobutyl)-phenol; (28) a solution of di-(m-dimethylaminophenyl)-phosphoryl chloride in isopropanol is treated with aqueous caustic soda to give di-(m-dimethylaminophenyl) sodium phosphate; (29) the di - (m p - dimethylaminophenyl) - phosphonyl chloride in (21) is replaced by the diethylamino compound; (30) tri-(m-diethylaminophenyl) thiophosphate is prepared by the method of (16); (31) and (32) di-(p-dimethylaminophenyl)-thiophosphoryl chloride is heated with di-n-butylamine or aniline; (33)-(36) benzene phosphorus oxydichloride is reacted in benzene in the presence of triethylamine with two molecular proportions of m-, o- or p-dimethylamino-or m-diethylamino-phenol to produce diaryl esters of benzenephosphonic acid; (37)-(39) the di-(m-dimethylaminophenyl) esters of heptane- and cyclohexane-phosphonic acids and the di-(o-dimethylaminomethylphenyl) ester of benzenephosphonic acid are analogously prepared; (40) the m-diethylaminophenyl ester of (p)-benzene-(p)-dimethylaminophosphinic acid is prepared by reacting benzene phosphorus oxydichloride successively with equimolecular proportions of m-diethylaminophenol and di-methylamine; (41) and (42) benzene phosphorus thiodichloride is reacted in benzene and isopropanol with sodium m-diethylaminophenate or o-dimethylaminomethylphenate to form esters of benzenethiophosphonic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US681102XA | 1949-02-07 | 1949-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB681102A true GB681102A (en) | 1952-10-15 |
Family
ID=22080468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2364/50A Expired GB681102A (en) | 1949-02-07 | 1950-01-30 | Aryl esters of acid phosphorus compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB681102A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1064510B (en) * | 1955-03-07 | 1959-09-03 | Bayer Ag | Process for the preparation of Arylthionophosphonsäureestern |
| US3291866A (en) * | 1962-12-22 | 1966-12-13 | Bayer Ag | Thiophosphoric acid esters |
-
1950
- 1950-01-30 GB GB2364/50A patent/GB681102A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1064510B (en) * | 1955-03-07 | 1959-09-03 | Bayer Ag | Process for the preparation of Arylthionophosphonsäureestern |
| US3291866A (en) * | 1962-12-22 | 1966-12-13 | Bayer Ag | Thiophosphoric acid esters |
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