JPS5944395A - Ｏ，ｓ−ジメチル−チオロ燐酸アミドの製造方法 - Google Patents
Ｏ，ｓ−ジメチル−チオロ燐酸アミドの製造方法Info
- Publication number
- JPS5944395A JPS5944395A JP58137886A JP13788683A JPS5944395A JP S5944395 A JPS5944395 A JP S5944395A JP 58137886 A JP58137886 A JP 58137886A JP 13788683 A JP13788683 A JP 13788683A JP S5944395 A JPS5944395 A JP S5944395A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- solvent
- organic solvent
- methylation
- 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
- 150000001408 amides Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 13
- 238000007069 methylation reaction Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 230000011987 methylation Effects 0.000 claims description 11
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229940050176 methyl chloride Drugs 0.000 claims description 5
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 4
- 150000008045 alkali metal halides Chemical class 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 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 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 235000011511 Diospyros Nutrition 0.000 claims description 2
- 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 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 241000723267 Diospyros Species 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 3
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910052776 Thorium Inorganic materials 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- -1 quincinols Chemical compound 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- CJKYMBLMHNAVFQ-UHFFFAOYSA-N C[S+]=P(N)(O)O Chemical compound C[S+]=P(N)(O)O CJKYMBLMHNAVFQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000168853 Coprosma grandifolia Species 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 244000236655 Diospyros kaki Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001465382 Physalis alkekengi Species 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 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
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823228868 DE3228868A1 (de) | 1982-08-03 | 1982-08-03 | Verfahren zur herstellung von o,s-dimethylthiolophosphorsaeureamid |
| DE3228868.9 | 1982-08-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5944395A true JPS5944395A (ja) | 1984-03-12 |
| JPH0363554B2 JPH0363554B2 (https=) | 1991-10-01 |
Family
ID=6169960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58137886A Granted JPS5944395A (ja) | 1982-08-03 | 1983-07-29 | Ｏ，ｓ−ジメチル−チオロ燐酸アミドの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4537730A (https=) |
| EP (1) | EP0104352B1 (https=) |
| JP (1) | JPS5944395A (https=) |
| BR (1) | BR8304127A (https=) |
| DD (1) | DD210282A5 (https=) |
| DE (2) | DE3228868A1 (https=) |
| DK (1) | DK353783A (https=) |
| IL (1) | IL69387A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01113154U (https=) * | 1988-01-27 | 1989-07-31 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA494562A (en) * | 1948-02-04 | 1953-07-21 | American Cyanamid Company | Carbamylalkyl phosphates and method of preparation |
| BE581598A (https=) * | 1958-08-12 | |||
| DE1210835B (de) * | 1964-07-02 | 1966-02-17 | Bayer Ag | Verfahren zur Herstellung von Amidothiolphosphorsaeureestern |
| US3309266A (en) * | 1965-07-01 | 1967-03-14 | Chevron Res | Insecticidal compositions containing oalkyl-s-alkyl phosphoroamidothioates and methods for killing insects therewith |
| US3670057A (en) * | 1969-11-10 | 1972-06-13 | Sumitomo Chemical Co | S(alkllthio ethyl) phosphorothioamidate |
| US3832425A (en) * | 1972-12-21 | 1974-08-27 | Chevron Res | N-acyl-o-hydrocarbylphosphoroamidothioate salts and process for making same |
-
1982
- 1982-08-03 DE DE19823228868 patent/DE3228868A1/de not_active Withdrawn
-
1983
- 1983-07-21 US US06/516,167 patent/US4537730A/en not_active Expired - Fee Related
- 1983-07-26 EP EP83107310A patent/EP0104352B1/de not_active Expired
- 1983-07-26 DE DE8383107310T patent/DE3361068D1/de not_active Expired
- 1983-07-29 JP JP58137886A patent/JPS5944395A/ja active Granted
- 1983-08-01 IL IL69387A patent/IL69387A/xx unknown
- 1983-08-01 DD DD83253606A patent/DD210282A5/de not_active IP Right Cessation
- 1983-08-02 BR BR8304127A patent/BR8304127A/pt not_active IP Right Cessation
- 1983-08-02 DK DK353783A patent/DK353783A/da not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01113154U (https=) * | 1988-01-27 | 1989-07-31 |
Also Published As
| Publication number | Publication date |
|---|---|
| DK353783A (da) | 1984-02-04 |
| US4537730A (en) | 1985-08-27 |
| IL69387A (en) | 1987-10-30 |
| BR8304127A (pt) | 1984-03-13 |
| DE3228868A1 (de) | 1984-02-09 |
| JPH0363554B2 (https=) | 1991-10-01 |
| DE3361068D1 (en) | 1985-11-28 |
| EP0104352A1 (de) | 1984-04-04 |
| IL69387A0 (en) | 1983-11-30 |
| EP0104352B1 (de) | 1985-10-23 |
| DK353783D0 (da) | 1983-08-02 |
| DD210282A5 (de) | 1984-06-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69403165T2 (de) | Verfahren zur Herstellung 1-substituierte-5(4H)-Tetrazolinone | |
| JPS5944395A (ja) | Ｏ，ｓ−ジメチル−チオロ燐酸アミドの製造方法 | |
| CA1101883A (en) | Process for separating mixtures of 3- and 4- nitrophthalic acid | |
| JPS60172975A (ja) | エリスロ−３−（３，４−メチレンジオキシフエニル）セリンの製造方法 | |
| US2721207A (en) | Process for the production of amino diols and intermediate products utilized in said process | |
| DE1795344A1 (de) | 3-Amino-isothiazole | |
| JPH02149550A (ja) | Ｎ―（２―カルボキシ―３’，４’―ジメトキシ―シンナモイル）―アンスラニル酸及びその製造方法 | |
| EP0211306A2 (en) | Process for producing iminoctadine tri-(alkylbenzenesulfonates) | |
| ATE346051T1 (de) | Verfahren zur synthese von hochreinem 3,5-diamino 6-(2, 3-dichlorophenyl)-1,2,4-triazin | |
| JP5092289B2 (ja) | 光学活性Ｎ−ｔｅｒｔ−ブチルカルバモイル−Ｌ−ｔｅｒｔ−ロイシンの製造方法 | |
| Bryans et al. | LXXX.—The nitration of benzylpyridines and the oxidation of benzylpiperidines | |
| US3419616A (en) | Preparation of ninhydrin | |
| US2744118A (en) | Phthalimidopropionylaminoethyl disulfide and preparation | |
| Baker et al. | XLI.—The nature of the alternating effect in carbon chains. Part XI. Further evidence on the substitution of benzylamine salts | |
| JPS6316375B2 (https=) | ||
| CA1183542A (en) | Process for making triazoles | |
| Tonari et al. | Synthesis and antibacterial activity of α-methylenecamphor and isophorone derivatives | |
| JP2546067B2 (ja) | メタンジホスホン酸化合物の製造方法 | |
| US3959379A (en) | Preparation of primary amines | |
| JPS5944349A (ja) | カルバミン酸クロライドの製造方法 | |
| JPH0439448B2 (https=) | ||
| CN115572747A (zh) | 托匹司他的制备方法 | |
| JPH01500906A (ja) | セファロスポリン誘導体の新規製造方法 | |
| CA2105411A1 (en) | Process for the preparation of 2-aryl-1,3-propanediols | |
| JPS60158182A (ja) | 置換されたキナゾリン‐２，４（１ｈ，３ｈ）‐ジオン類の製造方法 |