GB808638A - Organic phosphoric acid triamides - Google Patents
Organic phosphoric acid triamidesInfo
- Publication number
- GB808638A GB808638A GB2460656A GB2460656A GB808638A GB 808638 A GB808638 A GB 808638A GB 2460656 A GB2460656 A GB 2460656A GB 2460656 A GB2460656 A GB 2460656A GB 808638 A GB808638 A GB 808638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethylene
- radical
- triamide
- formula
- acid binding
- 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
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical class NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 title abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- -1 pyrrolidino, hexamethyleneimino, morpholino Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000011230 binding agent Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000004986 diarylamino group Chemical group 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
- 239000004033 plastic Substances 0.000 abstract 2
- 229920003023 plastic Polymers 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07F9/553—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
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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
Compounds of the formula <FORM:0808638/IV (a)/1> wherein the radical <FORM:0808638/IV (a)/2> is a dialkylamino, alkylarylamino, diarylamino, pyrrolidino, hexamethyleneimino, morpholino, or piperidino radical, and X is oxygen or sulphur (see Group IV (b)) may be polymerized to form new plastics.ALSO:The invention comprises compounds of the formula <FORM:0808638/IV (b)/1> wherein the radical <FORM:0808638/IV (b)/2> is a dialkylamino, alkyl-aryl-amino, diarylamino, pyrrolidino, hexamethyleneimino-, morpholino or piperidino radical, and X is oxygen or sulphur. They may be obtained by reacting in the presence of an acid binding agent a compound of the formula <FORM:0808638/IV (b)/3> with ethyleneimine, the radical <FORM:0808638/IV (b)/4> and X being as defined above and Hal being chlorine or bromine. The reaction may be carried out in an inert solvent, e.g. benzene, ligroin, petroleum ether, carbon tetrachloride, ether, or dioxane, and suitable acid binding agents are tertiary amines, e.g. triethylamine, dimethylaniline, and pyridine, also ammonia or primary or secondary amines. The amines may serve simultaneously as solvents. Some of the halogeno phosphorus compounds may also be reacted in an aqueous or alcoholic medium in which case alkali metal hydroxides or carbonates may be used as acid binding agents. If the reaction is carried out in aqueous solution the product is preferably recovered from the aqueous medium by extraction with an organic solvent. Examples are given for the production of (1) N-dimethylene-N1,N1,N11,N11-tetraethyl phosphoric triamide; (2) N-dimethylene-N1,N11-bis - pentamethylene - phosphoric triamide; (3) N - dimethylene - N1 - pentamethylene - N11-3 - oxapentamethylenephosphoric triamide; (4) N - dimethylene - N1,N1,N11,N11 - tetramethylthiophosphoric triamide; and (5) N-dimethylene - N1,N11 - di - 3 - oxapentamethylene phosphoric triamide. The phosphoric acid derivatives dissolve or mix easily with water and hydroxylated solvents and with the usual organic solvents but the thiophosphoric derivatives are generally miscible only with hydrocarbons, ethers and dimethylformamide. The products may be used for treating textile materials, as therapeutic agents since they show the capacity to prevent the growth of malignant tumours in animals and may also be polymerized to yield new plastics.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2460656A GB808638A (en) | 1956-08-10 | 1956-08-10 | Organic phosphoric acid triamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2460656A GB808638A (en) | 1956-08-10 | 1956-08-10 | Organic phosphoric acid triamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808638A true GB808638A (en) | 1959-02-11 |
Family
ID=10214303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2460656A Expired GB808638A (en) | 1956-08-10 | 1956-08-10 | Organic phosphoric acid triamides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB808638A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3111526A (en) * | 1958-10-23 | 1963-11-19 | Philips Corp | Certain phosphorus amide derivatives of imidazoles |
| US3227611A (en) * | 1958-10-23 | 1966-01-04 | Philips Corp | Method of combatting plant harmful organisms |
-
1956
- 1956-08-10 GB GB2460656A patent/GB808638A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3111526A (en) * | 1958-10-23 | 1963-11-19 | Philips Corp | Certain phosphorus amide derivatives of imidazoles |
| US3227611A (en) * | 1958-10-23 | 1966-01-04 | Philips Corp | Method of combatting plant harmful organisms |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES8200357A1 (en) | Process for the production of sulphenamides. | |
| GB808638A (en) | Organic phosphoric acid triamides | |
| GB823709A (en) | Manufacture of a triazine derivative | |
| ES212646A2 (en) | Preparation of 2-benzothiazolyl sulfene morpholide | |
| GB816286A (en) | Thiophosphoric acid esters and process for their manufacture | |
| GB1055184A (en) | A process for the manufacture of 2-styryl-oxazole compounds | |
| GB852384A (en) | Process for preparing dihydroxy alkyl acrylates and methacrylates | |
| JPS5622761A (en) | Novel 2,2'-bis(4-cumylphenol)derivative | |
| GB921536A (en) | Substituted n-hydroxyureas and a process for their manufacture | |
| GB902058A (en) | Process for the preparation of di-benzoxazolyl-ethylene compounds | |
| GB894428A (en) | Process for the manufacture of basically substituted phthalazines | |
| GB1043502A (en) | New betaines and process for their manufacture | |
| GB1346475A (en) | Process for the production of substituted thionophosphoryl chlorides | |
| FR1195350A (en) | Process for the manufacture of water-soluble organic compounds containing triazine nuclei | |
| GB864632A (en) | Thionophosphonic acid esters | |
| GB754295A (en) | Preparation of ª -chloro-ª -methyl aliphatic acids and acid chlorides | |
| GB929216A (en) | Process for the production of thiol-and thionothiol-phosphoric and -phosphinic acid esters | |
| ES450028A1 (en) | Desoxystreptamine derivative and its salts processes for preparing these compounds and pharmaceutical compositions containing them | |
| GB916063A (en) | New polymeric materials | |
| GB786763A (en) | Derivatives of thiophosphoric acid | |
| GB1024660A (en) | Novel heterocyclic compounds containing sulphur and nitrogen as hetero atoms and a process for their manufacture | |
| GB771317A (en) | Nicotinamide ascorbate and process for making the same | |
| GB865844A (en) | Organic phosphorus compounds and process for preparing same | |
| IE38930B1 (en) | Production of 2,5-disubstituted benzamides | |
| GB854443A (en) | New phosphorus-containing ethylene-imine derivatives and process for their manufacture |