SU222358A1 - METHOD OF OBTAINING S, K'-LISDIALCOXYPHOSPHORYL - Google Patents
METHOD OF OBTAINING S, K'-LISDIALCOXYPHOSPHORYLInfo
- Publication number
- SU222358A1 SU222358A1 SU1131375A SU1131375A SU222358A1 SU 222358 A1 SU222358 A1 SU 222358A1 SU 1131375 A SU1131375 A SU 1131375A SU 1131375 A SU1131375 A SU 1131375A SU 222358 A1 SU222358 A1 SU 222358A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzene
- lisdialcoxyphosphoryl
- obtaining
- acetone
- calculated
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N Sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SJLRLJGNDKYTLV-UHFFFAOYSA-N CCN(CC)P(O)=O Chemical compound CCN(CC)P(O)=O SJLRLJGNDKYTLV-UHFFFAOYSA-N 0.000 description 1
- -1 Diethoxyphosphoryl sulfamide Chemical compound 0.000 description 1
- FXZWPZMCZNJILD-UHFFFAOYSA-N N-[(6-bromopyridin-3-yl)methyl]ethanamine;hydrochloride Chemical compound Cl.CCNCC1=CC=C(Br)N=C1 FXZWPZMCZNJILD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003012 phosphoric acid amides Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Description
Насто щее изобретение относитс к способу получени не описанных ранее М,Ы-бйсдиалкоксифосфорилсульфамидов , которые могут «айти применение как лекарственные препараты или дохимикаты.The present invention relates to a process for the preparation of M, N-bysdialkoxyphosphoryl sulphamides not previously described, which can be used as medicaments or prechemicals.
Предлагаемый способ основан на взаимодействии амидов диалкилфосфорных кислот с хлористым сульфурилом в присутствии основани , например триэтиламина, в среде инертного растворител , например бензола.The proposed method is based on the interaction of dialkyl phosphoric acid amides with sulfuryl chloride in the presence of a base, for example, triethylamine, in an inert solvent, for example benzene.
Пример. Дл получени М,М-би€Диэтоксифосфорилсульфамида к бензольному раствору 10,71 г (0,07 моль) амида диэтилфосфо:рной кислоты и 7,07 г (0,07 моль) триэтиламина прибавл ют бензольный раствор 4,72 г (0,035 моль) хлористого сульфурила при температуре- 10-ь5°С. Смесь перемешивают в течение 2 час при 20°С. Осадок выделившегос продукта вместе с хлоргидратом амина отфильтровывают и последний отмывают водой. Из бензольного фильт|рата после удалени растворител получают дополнительное количество кристаллического продукта. Обший выход 6,4 г (50% от теоретического), Вешество, перекристаллизованное из ацетона, имеет вид мелких иголочек. Т. пл, 151-152°С.Example. To obtain M, M-Bi Diethoxyphosphoryl sulfamide, a benzene solution of 4.72 g (0.035 mol) is added to a benzene solution of 10.71 g (0.07 mol) of diethylphosphonic acid amide and 7.07 g (0.07 mol) of triethylamine. ) chloride sulphuryl at a temperature of 10 -5 ° C. The mixture is stirred for 2 hours at 20 ° C. The precipitate of the separated product is filtered off with amine hydrochloride and the latter is washed with water. After removal of the solvent, an additional amount of crystalline product is obtained from the benzene filtrate. The total yield is 6.4 g (50% of the theoretical). The substance, recrystallized from acetone, has the form of small needles. T. pl, 151-152 ° C.
Найдено, %: РFound%: P
16,75, 16.75,
Csll2- N.iOsP2S.Csll2- N.iOsP2S.
Вычислено, %: Р 16,84.Calculated,%: R 16.84.
Веш,ество раствор етс в спирте, при нагревании в бензоле, ацетоне, хлороформе, умеренно раствор етс в воде, не раствор етс в эфире.Suspension dissolves in alcohol, when heated in benzene, acetone, chloroform, moderately soluble in water, not soluble in ether.
Аналогично получают другие Ы,М-бисдиалкоксифосфо ,рил сульфамиды:Similarly, other S, M-bisdialkoxyphospho, ryl sulfamides are obtained:
R -изо-СзН7(11). Т. пл, 132-133 С (ацетон и петролейный эфир), выход 37,7%. Найдено, %: Р 14,71. Ci.H.soN.OsPaS. Вычислено, %: Р 14,61, R -С Н7(П1), Т, пл, 149-150 0 (ксилол), выход 42%. Найдено, %: Р 14,49,R-iso-SzN7 (11). So pl, 132-133 C (acetone and petroleum ether), yield 37.7%. Found,%: R 14.71. Ci.H.soN.OsPaS. Calculated,%: R 14.61, R -C H7 (P1), T, mp, 149-150 0 (xylene), yield 42%. Found,%: R 14.49,
Oi2H:3oN2O8P.S.Oi2H: 3oN2O8P.S.
Вычислено, %: Р 14,61. R -04H9(IV). Т, пл. 138-139 0 (лигроин), выход 33,3%.Calculated,%: R 14.61. R-04H9 (IV). T, pl. 138-139 0 (ligroin), yield 33.3%.
Найдено, %: Р 12,95. OioHssNoOgPgS. Вычислено; %: Р 12,9. Ооединени при R - (II-IV) - раствор ютс в бензоле, хлороформе, ацетоне, ксилоле , не раствор ютс в воде и эфире. 3 Предмет изобретени Способ получени М,К-бисдиалкоксифОСфОрилсульфамидов , отличающийс тем, что амиды диалкилфосфорных кислот .подвергают 5 4 взаимодействию с хлористым сульф;урилом в присутствии основани , нанример триэтиламина , в среде инертного растворител , наП|ример бензола, Found,%: P 12.95. OioHssNoOgPgS. Calculated; %: P 12.9. Compounds at R - (II-IV) - are dissolved in benzene, chloroform, acetone, xylene, not soluble in water and ether. 3 Subject of the invention. A method for producing M, K-bisdialkoxyfosphoryl sulphamides, characterized in that dialkylphosphoric acid amides are reacted with 4-4 with chloride sulphide; uril in the presence of a base, such as triethylamine, in an inert solvent, Phenol | benzene,
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU222358A1 true SU222358A1 (en) |
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