SU248680A1 - METHOD OF OBTAINING p-A ^ KIL (Aryl) -sulfonyl-hydrazides 0-Alkyl, O-Alkyl (aryl) -phosphorus or thiophosphoric acids - Google Patents
METHOD OF OBTAINING p-A ^ KIL (Aryl) -sulfonyl-hydrazides 0-Alkyl, O-Alkyl (aryl) -phosphorus or thiophosphoric acidsInfo
- Publication number
- SU248680A1 SU248680A1 SU1255090A SU1255090A SU248680A1 SU 248680 A1 SU248680 A1 SU 248680A1 SU 1255090 A SU1255090 A SU 1255090A SU 1255090 A SU1255090 A SU 1255090A SU 248680 A1 SU248680 A1 SU 248680A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- aryl
- sulfonyl
- hydrazides
- kil
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 7
- 150000003582 thiophosphoric acids Chemical class 0.000 title claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 229940042795 Hydrazides for tuberculosis treatment Drugs 0.000 claims description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 235000015450 Tilia cordata Nutrition 0.000 claims 1
- 235000011941 Tilia x europaea Nutrition 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000004571 lime Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- JNONJXMVMJSMTC-UHFFFAOYSA-N hydron;triethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)CC JNONJXMVMJSMTC-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- -1 sulfonyl hydrates Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к способу получени не описанных в литературе сульфонилгидратов О-алкил, О-алкил(арил)-фосфорных или тиофосфорных кислот общей формулыThe invention relates to a process for the preparation of sulfonyl hydrates not described in literature. O-alkyl, O-alkyl (aryl) -phosphoric or thiophosphoric acids of the general formula
(RO) (RO) Р (X) NnNHSOsR.(RO) (RO) P (X) NnNHSOsR.
где R-алкил R, R - алкил, арил; X - О или S.where R is alkyl R, R is alkyl, aryl; X - O or S.
Эти соединени могут быть использованы в качестве пестицидов.These compounds can be used as pesticides.
Способ основан на реакции гидразидов О-алкил, О-алкил(ар1ил)-фосфорных или тиофосфорных кислот с сульфохл01рида,ми в ирисутствии акцептора хлористого водорода, нанример триэтиламина, в среде инертного органического растворител , например в бензоле, с последующим выделением нродукта известными приемами. Процесс ведут при 30-37°С.The method is based on the reaction of hydrazides O-alkyl, O-alkyl (ar1yl) -phosphoric or thiophosphoric acids with sulfochloride, in the presence of a hydrogen chloride acceptor, using triethylamine, in an inert organic solvent, for example in benzene, followed by separation of the product with known methods. The process is conducted at 30-37 ° C.
Чистоту получаемых соединений провер ют методом тонкослойной хроматографии, строение их доказано ИК-спектрами.The purity of the compounds obtained was checked by thin layer chromatography, their structure was proved by IR spectra.
Пример. Получение (3-фенилсульфонилгидразида 0,О-диэтилтиофосфорной кислоты.Example. Preparation of (3-phenylsulfonylhydrazide 0, O-diethylthiophosphoric acid.
К раствору 0,03 моль гидразида О,0-диэтилтиофосфорной кислоты в 70 мл бензола с 0,03 моль триэтиламинов при 20°С прибавл ют раствор 0,03 моль толуолсульфохлорида вTo a solution of 0.03 mol of hydrazide O, 0-diethylthiophosphoric acid in 70 ml of benzene with 0.03 mol of triethylamines at 20 ° C was added a solution of 0.03 mol of toluene sulfonyl chloride in
30 мл бензола. При этом наблюдаетс экзотермическа реакци . Реакционную массу перемешивают при 30-37°С 5 час. Выпавший сол нокислый триэтиламин отфильтровывают.30 ml of benzene. An exothermic reaction is observed. The reaction mass is stirred at 30-37 ° C for 5 hours. Triethylamine sulphate precipitated is filtered off.
Фильтрат дважды промывают водой, сушат над . Бензол отгон ют. Остаток (кристаллы ) дважды перекристаллизовывают из бензола. Чистоту полученного продукта провер ют методом тонкослойной хроматографии.The filtrate is washed twice with water, dried over. The benzene is distilled off. The residue (crystals) is recrystallized twice from benzene. The purity of the obtained product was checked by thin layer chromatography.
Т. пл. 124-127°С. Выход 53% (от теорнн).T. pl. 124-127 ° C. Output 53% (from the theory).
Аналогично получают соединени , приведенные в таблице.The compounds listed in the table are prepared analogously.
Предмет изобретени Subject invention
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU248680A1 true SU248680A1 (en) |
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