SU491637A1 - Method for preparing 2-dialkylamino-3-aryl-4-oxo-1,3,2-thiaazaphospholanes - Google Patents

Method for preparing 2-dialkylamino-3-aryl-4-oxo-1,3,2-thiaazaphospholanes

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Publication number
SU491637A1
SU491637A1 SU2039256A SU2039256A SU491637A1 SU 491637 A1 SU491637 A1 SU 491637A1 SU 2039256 A SU2039256 A SU 2039256A SU 2039256 A SU2039256 A SU 2039256A SU 491637 A1 SU491637 A1 SU 491637A1
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SU
USSR - Soviet Union
Prior art keywords
thiaazaphospholanes
dialkylamino
oxo
aryl
preparing
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Application number
SU2039256A
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Russian (ru)
Inventor
Лев Ильич Мизрах
Лидия Юльевна Полонская
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Институт биофизики
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Priority to SU2039256A priority Critical patent/SU491637A1/en
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Publication of SU491637A1 publication Critical patent/SU491637A1/en

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Description

1one

Изобретение относитс  к способу получени  новых фосфорорганических соединений, которые могут найти применение в качестве полупродуктов синтеза биологически активных веществ, а также присадок к маслам.The invention relates to a method for producing new organophosphorus compounds that can be used as intermediates for the synthesis of biologically active substances, as well as additives to oils.

Известны тиаазафосфоланы, незамещенные в третьем и четвертом положении или замещенные в третьем иоложении алкильной группой .Known are thiazaphospholanes, unsubstituted in the third and fourth position, or substituted in the third grade by an alkyl group.

Из числа соединений подобного типа, в которых азот цикла был бы соединен с карбонильной группой, известны лишь полученные недавно 2-диалкиламино - 3 - ацил-1,3,2-оксаазафосфоланы , которые получают взаимодействием гексаэтилтриамида фосфористой кисЛОТЫ с «-ацетиламиноэтанолом.Among the compounds of this type in which the nitrogen of the cycle would be combined with a carbonyl group, only recently obtained 2-dialkylamino-3-acyl-1,3,2-oxa-azaphospholanes are obtained, which are obtained by the interaction of hexaethyl triamide phosphorous acid with α-acetylaminoethanol.

Принципиальное отличие соединений заключаетс  в том, что в этих соединени х карбонил , св занный с азотом, находитс  в боковой цени, тогда как в соедииени х, нолучаемых по предлагаемому методу, карбонильна  группа включена в цикл.The principal difference between the compounds is that in these compounds the carbonyl bonded to nitrogen is in the lateral value, whereas in compounds obtained by the proposed method, the carbonyl group is included in the cycle.

Таким образом получены соединени  новой неизвестной ранее структуры одновременной реакцией меркаптолиза и переамидировани  амидофосфатов, котора  ранее дл  амидов КИСЛОТ трехвалентного фосфора не была известна .In this way, compounds of a previously unknown previously obtained structure were obtained by the simultaneous reaction of mercaptolysis and transamidation of amidophosphates, which previously was not known for trihydric phosphorus amides.

Согласно изобретению, описываетс  способ получеии  2-диалкиламино-3-арил-4-от-ссо-1, 3, According to the invention, a process for the preparation of 2-dialkylamino-3-aryl-4-ot-cso-1, 3 is described,

2-тиаазафосфоланов взаимодействием гексаалкилтриамида фосфористой кислоты с моиоариламидами тиогликолевой кислоты.2-thiaazaphospholanes by the interaction of hexa-alkyl triamide of phosphorous acid with thioglycolic acid aryoamylamides.

Предлагаемый способ позвол ет получать фосфорсодержащие гетероциклы, содержащие в четвертом положении оксогруппу, следующего строени The proposed method allows to obtain phosphorus-containing heterocycles containing an oxo group in the fourth position, the following structure

Г-ГYr

.N-Ar.N-ar

та 2that 2

где R - алкил; Аг - незамещенный или замещенный феиил.where R is alkyl; Ar - unsubstituted or substituted feiil.

Процесс ведут при повыщенной температуре 100-130° С с последующим выделением целевого продукта известными приемами.The process is carried out at an elevated temperature of 100-130 ° C, followed by separation of the target product by known techniques.

При м е р. Эквимол рные количества гексаалкилтриамида фосфористой кислоты и моноариламида тиогликолевой кислоты нагревают при перемешивании и 100-130° С с одновременной отгонкой выдел ющегос  диалкиламина . Нагревание ведут до тех пор, пока не отгонитс  около 75% расчетного количества диалкиламина (из расчета 2 мол  диалкиламина на 1 моль вз того в реакцию гексаалкилтриамидофосфита ), удал ют в вакуумеAn example. Equimolar amounts of hexaalkyltriamide of phosphorous acid and thioglycolic acid monoarylamide are heated with stirring at 100-130 ° C with simultaneous distillation of the liberated dialkylamine. Heating is carried out until about 75% of the calculated amount of dialkylamine is distilled off (at the rate of 2 mol of dialkylamine per 1 mol of hexaalkyltriamidophosphite reacted), removed in vacuum

остатки диалкиламина и оставшуюс  массу фракционируют.the dialkylamine residues and the remaining mass are fractionated.

Из 12,35 г гексаэтилтриамида фосфористой кислоты и 8,35 г анилида тиогликолевой кислоты получают 8,5 г (63,4%) 2-диэтиламино-Зфеиил-4-оксо-1 ,3,2 - тиаазафосфолана. Т. кип. 99--10ГС (0,015); т. пл. 43-45°С.From 12.35 g of phosphorous acid hexaethyl triamide and 8.35 g of thioglycolic anilide anhydride, 8.5 g (63.4%) of 2-diethylamino-Cfeiyl-4-oxo-1, 3,2-thiaazaphospholane are obtained. T. Kip. 99--10ГС (0,015); m.p. 43-45 ° C.

Найдено, %: С 53,62; 53,49; Н 6,58; 6,59; Р 11,54; 11,68; N 10,42; 10,56; S 11,51; 11,73.Found,%: C 53.62; 53.49; H 6.58; 6.59; R 11.54; 11.68; N 10.42; 10.56; S 11.51; 11.73.

Ci2Hl7N2OPS.Ci2Hl7N2OPS.

Вычислено, %; С 53,70; Н 6,35; Р 11,55; N 10,42; S 11,90.Calculated,%; C 53.70; H 6.35; R 11.55; N 10.42; S 11.90.

Форм у л а и 3 о б Р е т е и и  Formula and 3 about B R e e and and

Claims (2)

1.Способ получени  2-дпалкила.мино-Зарил-4-OKCo-l , 3, 2 - тиаазафосфоланов, отлич а ю щ и и с   тем, что гексаалкилтриамид фосфористой кислоты подвергают взаимодействию с моноариламидом тиогликолевой кислоты при повышенной температуре с иоследуюидим выделением це.тевого продукта известны .ми приемами.1. A method for the preparation of 2-dipalkyl.mino-Zaryl-4-OKCo-l, 3, 2 - thiaazaphospholanes, is distinguished by the fact that hexaalkyltriamide phosphorous acid is reacted with thioglycolic monoarylamide at elevated temperature, followed by release of the This product is known for its methods. 2.Способ по п. 1, о T;I и ч а ю ш, и и с   тем, что процесс ведут при 100-130°С.2. The method according to claim 1, T T; I and h and w and so that the process is carried out at 100-130 ° C.
SU2039256A 1974-07-01 1974-07-01 Method for preparing 2-dialkylamino-3-aryl-4-oxo-1,3,2-thiaazaphospholanes SU491637A1 (en)

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SU2039256A SU491637A1 (en) 1974-07-01 1974-07-01 Method for preparing 2-dialkylamino-3-aryl-4-oxo-1,3,2-thiaazaphospholanes

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Application Number Priority Date Filing Date Title
SU2039256A SU491637A1 (en) 1974-07-01 1974-07-01 Method for preparing 2-dialkylamino-3-aryl-4-oxo-1,3,2-thiaazaphospholanes

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SU491637A1 true SU491637A1 (en) 1975-11-15

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