IL131625A - Process to form a noble N - noble derivative of S, O - dialkyl phosphoramidate - Google Patents
Process to form a noble N - noble derivative of S, O - dialkyl phosphoramidateInfo
- Publication number
- IL131625A IL131625A IL13162599A IL13162599A IL131625A IL 131625 A IL131625 A IL 131625A IL 13162599 A IL13162599 A IL 13162599A IL 13162599 A IL13162599 A IL 13162599A IL 131625 A IL131625 A IL 131625A
- Authority
- IL
- Israel
- Prior art keywords
- phosphoroamidothioate
- methyl
- dialkyl
- acyl derivative
- alcohol
- Prior art date
Links
- RJBIAAZJODIFHR-UHFFFAOYSA-N dihydroxy-imino-sulfanyl-$l^{5}-phosphane Chemical compound NP(O)(O)=S RJBIAAZJODIFHR-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 16
- 238000005917 acylation reaction Methods 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- MINHJPWDPAMUSK-UHFFFAOYSA-N [amino(methylsulfanyl)phosphoryl]oxyethane Chemical compound CCOP(N)(=O)SC MINHJPWDPAMUSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 125000003047 N-acetyl group Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 231100000606 suspected carcinogen Toxicity 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
-
- 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
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2487—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-C(=X) (X = O, S, Se; n = 0, 1)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/143,769 US5973180A (en) | 1998-08-31 | 1998-08-31 | Process for the production of an N-acyl derivative of O,S-dialkyl phosphoroamidothioate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL131625A0 IL131625A0 (en) | 2001-01-28 |
| IL131625A true IL131625A (en) | 2002-11-10 |
Family
ID=22505530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13162599A IL131625A (en) | 1998-08-31 | 1999-08-27 | Process to form a noble N - noble derivative of S, O - dialkyl phosphoramidate |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5973180A (pt) |
| EP (1) | EP0984017A3 (pt) |
| JP (1) | JP2000072786A (pt) |
| KR (1) | KR20000017154A (pt) |
| CN (1) | CN1248582A (pt) |
| AR (1) | AR020344A1 (pt) |
| BR (1) | BR9904474A (pt) |
| CA (1) | CA2280381C (pt) |
| CO (1) | CO5221044A1 (pt) |
| IL (1) | IL131625A (pt) |
| TR (1) | TR199902086A2 (pt) |
| ZA (1) | ZA995559B (pt) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100360545C (zh) * | 2002-06-07 | 2008-01-09 | 武汉化工学院 | 有机磷酰胺盐酸盐 |
| CN1931864B (zh) * | 2005-09-18 | 2010-05-05 | 李坚 | 高含量甲胺磷和高含量乙酰甲胺磷的制备 |
| CN106496061B (zh) * | 2016-10-20 | 2018-06-05 | 湘潭大学 | 一种萃取分离酰化反应液中乙酰精胺的方法 |
| US10669295B2 (en) * | 2018-07-19 | 2020-06-02 | Arysta Lifescience Inc. | Process for preparation of O,O-dimethyl phosphoramidothioate and N-(methoxy-methylsulfanylphosphoryl) acetamide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3716600A (en) * | 1970-02-24 | 1973-02-13 | Chevron Res | N-acyl derivatives of phosphoroamidothioates |
| US3775519A (en) * | 1971-06-28 | 1973-11-27 | Chevron Res | Preparation of phosphoroamido-thionate by ketene acylation |
| US3732344A (en) * | 1971-07-21 | 1973-05-08 | Chevron Res | Preparation of phosphoroamidothionate by anhydride acylation |
-
1998
- 1998-08-31 US US09/143,769 patent/US5973180A/en not_active Expired - Lifetime
-
1999
- 1999-08-06 KR KR1019990032349A patent/KR20000017154A/ko not_active Application Discontinuation
- 1999-08-17 CA CA002280381A patent/CA2280381C/en not_active Expired - Lifetime
- 1999-08-24 JP JP11236662A patent/JP2000072786A/ja active Pending
- 1999-08-27 IL IL13162599A patent/IL131625A/en not_active IP Right Cessation
- 1999-08-27 AR ARP990104313A patent/AR020344A1/es unknown
- 1999-08-27 TR TR1999/02086A patent/TR199902086A2/xx unknown
- 1999-08-27 EP EP99116737A patent/EP0984017A3/en not_active Withdrawn
- 1999-08-30 CO CO99054774A patent/CO5221044A1/es not_active Application Discontinuation
- 1999-08-30 ZA ZA9905559A patent/ZA995559B/xx unknown
- 1999-08-31 BR BR9904474-9A patent/BR9904474A/pt not_active IP Right Cessation
- 1999-08-31 CN CN99118407A patent/CN1248582A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2280381C (en) | 2009-11-03 |
| CO5221044A1 (es) | 2002-11-28 |
| BR9904474A (pt) | 2000-09-19 |
| IL131625A0 (en) | 2001-01-28 |
| KR20000017154A (ko) | 2000-03-25 |
| EP0984017A2 (en) | 2000-03-08 |
| TR199902086A2 (xx) | 2000-03-21 |
| AR020344A1 (es) | 2002-05-08 |
| JP2000072786A (ja) | 2000-03-07 |
| CA2280381A1 (en) | 2000-02-29 |
| US5973180A (en) | 1999-10-26 |
| ZA995559B (en) | 2000-04-04 |
| EP0984017A3 (en) | 2001-05-16 |
| CN1248582A (zh) | 2000-03-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5138084A (en) | Process for the preparation of 4-o-phosphates of dopamine and dopamine derivatives | |
| SU1149873A3 (ru) | Способ получени трео-2-окси-3-(4-метоксифенил)-3-(2-нитрофенилтио)пропионового сложного эфира и его вариант | |
| KR930011283B1 (ko) | 3'-아지도-3'-디옥시디미딘 및 그 유사화합물의 합성방법 | |
| US5973180A (en) | Process for the production of an N-acyl derivative of O,S-dialkyl phosphoroamidothioate | |
| EP0950664B1 (en) | Process for producing N-glycyltyrosine | |
| AU779799B2 (en) | Method for production of N-phosphonomethylglycine | |
| JP3901321B2 (ja) | リボフラビン−５’−リン酸またはそのナトリウム塩の製造法 | |
| MXPA99007904A (en) | Improved procedure for the production of an n-acid derivative of fosforoamidotioato de o, -dialqu | |
| US4585863A (en) | Process for the manufacture of 2-isopropyl-4-methyl-6-hydroxypyrimidine | |
| EP0703238A1 (en) | A method for purifying O,S-dimethyl N-acetylphosphoramidothioate | |
| US5215973A (en) | Optically active and racemic hydrated diacetylesters of α-glycero-phosphoryl-choline | |
| EP0070467B1 (en) | Process for synthesising n-isopropyl-n'-o-carbomethoxyphenylsulphamide | |
| EP0502357A1 (en) | Optically active and racemic hydrated diacetylesters of alpha-glycero-phosphoryl-choline | |
| US4313894A (en) | Process for the production of 3-cyanopropionamide | |
| US4515958A (en) | Process for preparing 1-alkyl-5-mercaptotetrazoles | |
| KR860001900B1 (ko) | β-클로로 아라닌의 제조법 | |
| US4256672A (en) | Process for the preparation of phosphoric esters and thiophosphoric esters | |
| JP2004532282A (ja) | Ｎ−ホスフォノメチルグリシンの製造方法 | |
| EP0853077B1 (en) | Process for producing alkyl 3-amino-4-substituted benzoates | |
| KR830001686B1 (ko) | 아미노 아릴티오포스페이트류 및 아미노아릴포스페이트류의 제조방법 | |
| CA1146968A (en) | 6-amino-1-hydroxyhexyliden diphosphonic acid, salts and a process for production thereof | |
| JP3619277B2 (ja) | ジヒドロポリプレニルモノホスフェートの製造方法及びその中間体化合物 | |
| EP0052903B1 (en) | Preparation of dihalovinylcyclopropane carboxylic acids | |
| US20040158082A1 (en) | Process for the preparation of isoflavones | |
| KR830000552B1 (ko) | 인산 에스테르류 및 티오인산 에스테르류의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |