SU387976A1 - METHOD OF OBTAINING 1,1-DYRILTS TRINITROETHYL ETHERAL ETHERS, ICL-PROPANKARBONIC ACIDS - Google Patents

METHOD OF OBTAINING 1,1-DYRILTS TRINITROETHYL ETHERAL ETHERS, ICL-PROPANKARBONIC ACIDS

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Publication number
SU387976A1
SU387976A1 SU1659754A SU1659754A SU387976A1 SU 387976 A1 SU387976 A1 SU 387976A1 SU 1659754 A SU1659754 A SU 1659754A SU 1659754 A SU1659754 A SU 1659754A SU 387976 A1 SU387976 A1 SU 387976A1
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SU
USSR - Soviet Union
Prior art keywords
trinitroethyl
acids
ethers
propankarbonic
dyrilts
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Application number
SU1659754A
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Russian (ru)
Inventor
А. Л. Фридман Ф. А. Габитов
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Publication date
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Priority to SU1659754A priority Critical patent/SU387976A1/en
Application granted granted Critical
Publication of SU387976A1 publication Critical patent/SU387976A1/en

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Изобретение относитс  :К способу получени  трниитроэтиловых зфиров 1,1-диарилцикло:прона .нкарбо«01вых кислот, которые представл ют интерес в качестве физиологически активных веществ, а также исходных соединений дл  синтеза различного класса нитросоедииений . Известен способ получени  пезамещенных эфиров диар,илциклои1ро1па«;карбоно:вых кислот взаимодействием диарилдиазометанов с Пезамещеи.ными эфара.ми непредельных к слот при -повышенных тем1нературах, например в кни н1:ем бензоле. Такой сиособ практически иеприемлем дл  синтеза тринитроэтиловых э фИр о,в 1,1-диарилциклоир.от аш арбоповых кислот, так как при повышенных темлературах наблюдаетс  нротекаиие побочных процессов , выходы продуктов значительно снижаютс . Дл  разработки способа получени  именно тринитроэтиловых эфиров 1,1-диарилциклоиропанкарбоновых кислот с высоким выходоМ нредложен способ, заключающийс  в том, что диарилдиазометаны, например дифенилдиазо .метап :и 9-диазофлуорен, .подвергают взаимодействию с тринитроэтиловым эфир.ом У-, / -ненасыщенной кислоты При температуре не выще 25°С. Ilporiecc ведут по схеме RCH CRCOOCHaC (NOs)3 + ГгСЫ. -О- - RCH-CR-С-OCHs-С (NO.) 3 где R Н; - CgHg, - COOCHaClNOsjs, R Н;-СНз,-CHsCOOCHs (N02) 3; R - C6H5,R2 бифенилен. Реакцию провод т смещением экви.молекул рных количеств днарилдиазометана (дифенилдиаз о метана, 9-диазофлуорена) и тринитроэтилового эфира J-, 3 -ненасыщеипо{1 кислоты в органическом растворителе (эфир, ацетон, бензол п т. д.) при 20-25°С. Циклонрапааовые производные выдел ют известными приемами. Полученные соединени  предСтавлены в таблице. Подробное осуществление процесса показано на следующих примерах. Пример 1. Синтез тринитроэтилового эфира 1,1-дифенилциклоиропан-2-карбоновой кислоты (I). К раствору 5 г свеженерегнанного тринитроэтилового эфира акриловой кислоты в 20 мл эфнра при перемещнвании и 20-25°С ирибавл ют раствор 4,2 г дифенилдиазометана is 30 мл эфира. Прн этом наблюдаетс  выделсние азота. Реакционную смесь выдерживаютThe invention relates to a method for the preparation of 1,1-diarylcyclo: pronecarcino-t-nitroethyl esters of lt acids, which are of interest as physiologically active substances, as well as starting compounds for the synthesis of a different class of nitrodiagenes. A known method for the preparation of di-esters of diar, ilcycloylpropyl; carbonic acid acids by the interaction of diaryl diazomethanes with pezameshtemi efarami unsaturated to slot at elevated temperature, for example, in benzene scintilla. This method is practically unsuitable for the synthesis of trinitroethyl compounds, in 1,1-diarylcycloir from your arbopic acids, since at elevated temperatures a number of side processes are observed, the yields of products are significantly reduced. In order to develop a process for the preparation of trinitroethyl ethers of 1,1-diarylcycloiropanecarboxylic acids with high yields, it is proposed that diaryl diazomethanes, e.g. acid At a temperature not higher than 25 ° C. Ilporiecc are conducted according to the scheme RCH CRCOOCHaC (NOs) 3 + GgSY. -O- - RCH-CR-C-OCHs-C (NO.) 3 where R H; - CgHg, - COOCHaClNOsjs, R N; -CH3, -CHsCOOCHs (N02) 3; R - C6H5, R2 biphenylene. The reaction is carried out by the displacement of equimolecular amounts of Dnaryldiazomethane (diphenyldiaz of methane, 9-diazofluorene) and trinitroethyl ester of J-, 3-unsaturated {1 acid in an organic solvent (ether, acetone, benzene, etc.) at 20-25 ° s Cycllonrapa derivatives are distinguished by known techniques. The compounds obtained are listed in the table. The detailed implementation of the process is shown in the following examples. Example 1. Synthesis of 1,1-diphenylcycloipropan-2-carboxylic acid trinitroethyl ester (I). A solution of 4.2 g of diphenyl diazomethane is 30 ml of ether to a solution of 5 g of freshly distilled trinitroethyl ester of acrylic acid in 20 ml of ethanol when displaced and 20-25 ° C. This is accompanied by nitrogen excretion. The reaction mixture is kept

SU1659754A 1971-05-24 1971-05-24 METHOD OF OBTAINING 1,1-DYRILTS TRINITROETHYL ETHERAL ETHERS, ICL-PROPANKARBONIC ACIDS SU387976A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU1659754A SU387976A1 (en) 1971-05-24 1971-05-24 METHOD OF OBTAINING 1,1-DYRILTS TRINITROETHYL ETHERAL ETHERS, ICL-PROPANKARBONIC ACIDS

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU1659754A SU387976A1 (en) 1971-05-24 1971-05-24 METHOD OF OBTAINING 1,1-DYRILTS TRINITROETHYL ETHERAL ETHERS, ICL-PROPANKARBONIC ACIDS

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SU387976A1 true SU387976A1 (en) 1973-06-22

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SU1659754A SU387976A1 (en) 1971-05-24 1971-05-24 METHOD OF OBTAINING 1,1-DYRILTS TRINITROETHYL ETHERAL ETHERS, ICL-PROPANKARBONIC ACIDS

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