JPS5839693A - １，３，３，５，５−ペンタハロ−１−チア−２，４，６−トリアザ−３，５−ジホスホリン−１−オキシドの製造法 - Google Patents
１，３，３，５，５−ペンタハロ−１−チア−２，４，６−トリアザ−３，５−ジホスホリン−１−オキシドの製造法Info
- Publication number
- JPS5839693A JPS5839693A JP13997781A JP13997781A JPS5839693A JP S5839693 A JPS5839693 A JP S5839693A JP 13997781 A JP13997781 A JP 13997781A JP 13997781 A JP13997781 A JP 13997781A JP S5839693 A JPS5839693 A JP S5839693A
- Authority
- JP
- Japan
- Prior art keywords
- water
- triaza
- oxide
- basic aqueous
- thia
- 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.)
- Granted
Links
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 239000012044 organic layer Substances 0.000 claims abstract description 8
- -1 phosphazene halide Chemical class 0.000 claims abstract description 8
- 239000010410 layer Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000243 solution Substances 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 abstract description 5
- 239000002585 base Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 239000002243 precursor Substances 0.000 abstract description 3
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 1
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000011369 resultant mixture Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000269821 Scombridae Species 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 238000000260 fractional sublimation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- NVTNQIBQPLGHGE-UHFFFAOYSA-N n,n-dibutylbutan-1-amine;hydrate Chemical compound [OH-].CCCC[NH+](CCCC)CCCC NVTNQIBQPLGHGE-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- QVOFCQBZXGLNAA-UHFFFAOYSA-M tributyl(methyl)azanium;hydroxide Chemical compound [OH-].CCCC[N+](C)(CCCC)CCCC QVOFCQBZXGLNAA-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13997781A JPS5839693A (ja) | 1981-09-04 | 1981-09-04 | １，３，３，５，５−ペンタハロ−１−チア−２，４，６−トリアザ−３，５−ジホスホリン−１−オキシドの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13997781A JPS5839693A (ja) | 1981-09-04 | 1981-09-04 | １，３，３，５，５−ペンタハロ−１−チア−２，４，６−トリアザ−３，５−ジホスホリン−１−オキシドの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5839693A true JPS5839693A (ja) | 1983-03-08 |
| JPH0220640B2 JPH0220640B2 (enrdf_load_stackoverflow) | 1990-05-10 |
Family
ID=15258068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13997781A Granted JPS5839693A (ja) | 1981-09-04 | 1981-09-04 | １，３，３，５，５−ペンタハロ−１−チア−２，４，６−トリアザ−３，５−ジホスホリン−１−オキシドの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5839693A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0257516A (ja) * | 1988-08-22 | 1990-02-27 | Yamada Kikai Kogyo Kk | ゴム紐による結束方法および装置 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03105666U (enrdf_load_stackoverflow) * | 1990-02-16 | 1991-11-01 |
-
1981
- 1981-09-04 JP JP13997781A patent/JPS5839693A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0257516A (ja) * | 1988-08-22 | 1990-02-27 | Yamada Kikai Kogyo Kk | ゴム紐による結束方法および装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0220640B2 (enrdf_load_stackoverflow) | 1990-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107963993A (zh) | 一种高纯度氟虫腈的制备方法 | |
| JPS5839693A (ja) | １，３，３，５，５−ペンタハロ−１−チア−２，４，６−トリアザ−３，５−ジホスホリン−１−オキシドの製造法 | |
| US6153765A (en) | Process for producing and method of crystallizing 2-azabicyclo(2.2.1)hept-5-en-3-one | |
| CN1064673C (zh) | 3,4－二羟基－5－硝基苯甲醛的制备方法 | |
| JP3409590B2 (ja) | Ｏ，ｏ−ジメチルホスホロアミドチオエートの製造法 | |
| JP4986343B2 (ja) | １−クロロカルボニルピペリジン誘導体塩酸塩の処理方法 | |
| JP4209022B2 (ja) | イソシアノ酢酸アルキルエステル類の製造法 | |
| JP4649590B2 (ja) | フェニルホスフィン酸メンチルの製造方法。 | |
| JPH037272A (ja) | 光学活性なテトラヒドロ―２―フロイックアシドの製造法 | |
| JPH03271273A (ja) | ２―クロロ―５―（アミノメチル）ピリジンの製造方法 | |
| JPS6365053B2 (enrdf_load_stackoverflow) | ||
| SU1625883A1 (ru) | Способ получени оксидов третичных арсинов | |
| KR100249783B1 (ko) | 염화 카보라노일의 제조방법 | |
| JPS61134367A (ja) | フエニルｎ−（２−ビフエニリルスルホニル）カ−バメ−トの改良製造方法 | |
| JP2771882B2 (ja) | Ｓ，ｏ―ジアルキル（２―オキソ―３―チアゾリジニル）ホスホノチオレートの製造法 | |
| JPS5820704A (ja) | １，３，３，５，５−ペンタハロ−１−チア−２，４，６−トリアザ−３，５−ジホスホリン−１−オキシドの分離方法 | |
| JPH0278692A (ja) | Ｓ，ｏ−ジアルキル（２−オキソ−３−チアゾリジニル）ホスホノチオレートの製造方法 | |
| JPS5832866A (ja) | 光学活性２−オキソイミダゾリジン−４−カルボン酸誘導体の製法 | |
| EP0484742A1 (en) | 2-Chloropropionaldehyde trimer and production process thereof | |
| CN115353437A (zh) | 一种顺-2-甲基-7-十八烯以及顺式-7,8-环氧-2-甲基十八烷的合成方法 | |
| DK156898B (da) | Fremgangsmaade til fremstilling af 2-arylpropionsyrer ved direkte kobling under anvendelse af et blandet magnesiumhalogenidkompleks | |
| JPH01213289A (ja) | フェロセンの製造方法 | |
| JP2003335786A (ja) | テトラキス（フッ化アリール）ボレート・エーテル錯体の製造方法 | |
| JPS6021148B2 (ja) | 光学的活性な新規ピリジニウム塩およびその製造方法 | |
| JPH07133246A (ja) | ４−ハロジフルオロメトキシネオフィル３−フェノキシベンジルエーテル類の改良された精製方法 |