SU236468A1 - - Google Patents
Info
- Publication number
- SU236468A1 SU236468A1 SU1183160A SU1183160A SU236468A1 SU 236468 A1 SU236468 A1 SU 236468A1 SU 1183160 A SU1183160 A SU 1183160A SU 1183160 A SU1183160 A SU 1183160A SU 236468 A1 SU236468 A1 SU 236468A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- thiophosphoric
- synthesis
- intermediates
- acids
- mixture
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- RYYWUUFWQRZTIU-UHFFFAOYSA-N thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic Effects 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 7
- 239000000543 intermediate Substances 0.000 claims 7
- 238000003786 synthesis reaction Methods 0.000 claims 7
- 230000002194 synthesizing Effects 0.000 claims 7
- 150000003582 thiophosphoric acids Chemical class 0.000 claims 5
- DJMQXCFMMJCCFN-UHFFFAOYSA-N benzyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(=S)CC1=CC=CC=C1 DJMQXCFMMJCCFN-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N Thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QVMHUALAQYRRBM-UHFFFAOYSA-N [P].[P] Chemical compound [P].[P] QVMHUALAQYRRBM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- -1 benzyl dithiophosphonates Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- UZZHGKFIGVRMNT-UHFFFAOYSA-O hydroxy-oxo-sulfanylphosphanium Chemical class O[P+](S)=O UZZHGKFIGVRMNT-UHFFFAOYSA-O 0.000 description 1
- 230000003364 opioid Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
Соединени , сиособу получени которых посв щено данное опиеанИе, можно нспользовать в качестве пестицидов.Compounds whose preparation method is dedicated to this opioid can be used as a pesticide.
Предлагаемый способ иолучени S-арил-Оалкнлбензилднтиофосфонатов общей формулыThe proposed method of obtaining S-aryl-Alkylbenzyl tertiophosphonates of the general formula
/SAr АгСН.,Р/ SAr AgSN., R
OR S OR S
где Аг и Аг - хлорзамещенный или незамещенный фенил, R - алкил с 1-4 С, основан на том, что S-арилбензнлхлордитиофосфонаты подвергают взаи.модейства1ю с нзбытком спирта в присутствии каталитических количеств солей эфиров тиофосфорных или тиофосфоновых кислот или полупродуктов их синтеза- п тисернистого фосфора и пиридина при нагревании до 65-120°С в течение 2-20 час с последующим выделением целевого продукта известными приемами. В качестве S-арилбензилхлордитиофосфоиатов можно исиользовать продукты взаимодействи тиофе.нолов и дихлорангидридов бензилтиофосфоиовых кислот.where Ar and Ar are chlorine substituted or unsubstituted phenyl, R is alkyl with 1-4 C, based on the fact that S-aryl benzyl chlorodithiophosphonates are interchanged with alcohol in the presence of catalytic amounts of salts of thiophosphoric or thiophosphonic acid esters or their intermediate products - grained phosphorus and pyridine when heated to 65-120 ° C for 2-20 hours, followed by separation of the target product by known methods. As S-arylbenzylchlordithiophosphoiates, it is possible to use the products of the interaction of thiophenol and dichlorohydrin benzylthiophosphoic acids.
Пример . S-Фенил-О-этилбеизилдитиофосфонат .An example. S-Phenyl-O-ethylbeisyl dithiophosphonate.
Смесь 0,05 г-моль дихлорацгидрида беизжптиофосфоновой кислоты, 0,05 г-моль тиофеиола , 50 мг п тисернистого фосфора и 80 мг пиридина выдерживают при 150-170°С, покаA mixture of 0.05 g-mol of bieuzhptiophosphonic acid dichlorohydride, 0.05 g-mol of thiofiol, 50 mg of n-colored phosphorous and 80 mg of pyridine are maintained at 150-170 ° C, while
не прекратитс выделение хлористого водорода . Реакционную массу выдерживают в вакууме при 10-15 мм рт. ст. и в остатке получают 5-феи11л бензил дитиохлорфосфонаг-в зкую жидкость. Выход 100%, пп 1,6660. Смесь 0,02 г-моль получеииого S-фенилбензилдитиохлорфосфоиата и 0,1 г моль этанола кии т т 12 час. Рсакциониую смесь выдерживают ири 10-15 лг.м рт. ст. п в остатке получают продукт в виде светлой масл нистой жидкости. по 1,6338; dl° 1.2340; MR о 89,25, выч. 89,48. Выход 100%.The release of hydrogen chloride will not cease. The reaction mass is maintained in vacuum at 10-15 mm RT. Art. and in the residue, 5-fei11l benzyl dithiochlorphosphonase viscous liquid is obtained. The yield is 100%, PP 1.6660. A mixture of 0.02 g-mol of the obtained S-phenylbenzyldithiochlorphospho-iata and 0.1 g of mol of ethanol is 12 hours. The reaction mixture is maintained at 10–15 lgmHg. Art. The residue in the residue gives the product as a light oily liquid. on 1,6338; dl ° 1.2340; MR of 89.25, cal. 89.48. The yield is 100%.
Найдено, %; Р 10,21; S 20,56.Found,%; P 10.21; S 20,56.
C,,HuOPS2.C ,, HuOPS2.
Вычислено, %: Р 10,06; S 20,79.Calculated,%: R 10.06; S 20.79.
П Р и м е Р 2. 5-2,5-Дихлорфенил-0-этилбензилдитиофосфонат .PREMI R 2. 5-2,5-Dichlorophenyl-0-ethylbenzyldithiophosphonate.
Смесь 0,02 г-моль 5-2,5-дихлорфенилбензилдитиохлорфосфоната (т. пл. 65-67°С), 0,1 г-моль этанола, 0,02 г п тисериистого фосфора и 0,03 г пиридина кип т т е обратным холодильником 12 час. Реакционную массу выдерживают в вакууме при 100°С/10- 15 мм рт. ст., в остатке получают продукт, который прп сто нии кристаллизуетс . Выход 100%, т. пл. 95-97°С (после промывю циклогексаном ).A mixture of 0.02 gmol of 5-2.5-dichlorophenylbenzyldithiochlorophosphonate (m.p. 65-67 ° C), 0.1 gmol of ethanol, 0.02 g of phosphorus phosphorus and 0.03 g of pyridine are boiled f reflux for 12 hours. The reaction mass is maintained in vacuum at 100 ° C / 10-15 mm Hg. Art., in the residue, a product is obtained which crystallizes. The yield is 100%, so pl. 95-97 ° C (after washing with cyclohexane).
Свойства бензилдитиофосфонатов ArCHoP/o. ,Properties of ArCHoP / o benzyl dithiophosphonates. ,
OROR
I ОЛГI OLG
VВычислепб ,- %: СГ 18,83; S 16,99. V Caliph, -%: SG 18.83; S 16.99.
Аналогично нолучены с количественным выходом соединени , свойства которых нриведеиы В таблице. Вещества № I, 2, 10 иолучеиы по методике примера 1, остальные - по методике примера 2.Similarly, compounds with a quantitative yield, the properties of which are listed in the table, were obtained with a quantitative yield. Substances number I, 2, 10 and the rays according to the method of example 1, the rest - according to the method of example 2.
Предмет изобретени Subject invention
Claims (3)
Publications (1)
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SU236468A1 true SU236468A1 (en) |
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