SU578861A3 - Method of preparing ureidophenoxy-2-oxy-3-aminopropanes - Google Patents

Method of preparing ureidophenoxy-2-oxy-3-aminopropanes

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Publication number
SU578861A3
SU578861A3 SU7201778355A SU1778355A SU578861A3 SU 578861 A3 SU578861 A3 SU 578861A3 SU 7201778355 A SU7201778355 A SU 7201778355A SU 1778355 A SU1778355 A SU 1778355A SU 578861 A3 SU578861 A3 SU 578861A3
Authority
SU
USSR - Soviet Union
Prior art keywords
hydroxy
residue
phenoxy
chj
ureidophenoxy
Prior art date
Application number
SU7201778355A
Other languages
Russian (ru)
Inventor
Вильхельм Макс
Original Assignee
Циба-Гейги А.Г., (Фирма)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Циба-Гейги А.Г., (Фирма) filed Critical Циба-Гейги А.Г., (Фирма)
Application granted granted Critical
Publication of SU578861A3 publication Critical patent/SU578861A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

В лнтератуте отсутствуют данные о получении соединений, указанной выше структурной формулы Г.There is no data on the receipt of the compounds of the above structural formula G.

Способ получени  новых уреидофенокси- -2-окси-3-аминопропанов в соответствии с изобретением заключаетс  в том, что основани  Шиффа структурной формулы Ни. И O-CHj-CH-CH-W-Rj O-CHj-CH-CHj-W iRj где RJ , R , R,, и R - имеют указанные выше значени , восстанавливают дигидри- дами легких металлов, например натрийбордигидридом , или каталитическим гидрированием в присутствии паллади , окиси платины или никел  Рене - При восстановлении необходимо следить за тем, чтобы в реакцию lie вступапи другие восстанавливаемые группы, в первую очередь, мочевйнна , избега  избытка восстановител  и соблюда  краткие сроки реакции. Реакцию провод т обычным образом в присутствии или отсутствии разбавителей, конденсационных и/или :каталитических средств, при пониженной, нормальной или повы шенной температуре, при необходимости в закрытом сосуде. Целевой продукт получают в свободном ввде ипи в виде солей.Так, например, можно получать основные, нейт- ральнь1е, смешенные соли или гидраты соле П р и м е р 1. 15 г 1-1и-.(Ы,и-ди t t - - t метилуреидо/-фенокси/-2-окси-3-аминопро-. пана К1т т т вместе с 150 мл ацетона в течение 3 ч. Раствор выпаривают, остаток раствор ют и добавл ют 2 г палпадневого угл  () при температуре 20 С и гт при нормальном давлении. По окончании пол лощени  водорода катализатор отфильтровывают и фильтрат высушивают досуха. Остаток раствор ют Б 1ОО мл 2 н . сол ной кислоты, нерастворившиес  части отфильтро вывают и экстрагируют хлористым .метиле- ном. Водну1р фазу довод т путем добавлени  2 к . едкого натра до щелочной реакции после чего экстрагируют хлористым метиленом . После выпаривани  растворител  остаетс  -(К ,н-диметилуреидо)фенокси| -2-окси-З-изопропиламинопропан струк турной формулыThe method for producing new ureidophenoxy-2-hydroxy-3-aminopropanes in accordance with the invention consists in the fact that Schiff bases of the structural formula No. And O-CHj-CH-CH-W-Rj O-CHj-CH-CHj-W iRj where RJ, R, R ,, and R - are as defined above, they are reduced by light metal dihydrides, for example, sodium borohydride, or catalytic by hydrogenation in the presence of palladium, platinum oxide or Rene nickel - When recovering, care must be taken to enter other recoverable groups in the lie reaction, first of all, urinary, avoid excess reducing agent and observe short reaction times. The reaction is carried out in the usual way in the presence or absence of diluents, condensation and / or catalytic agents, at low, normal or elevated temperature, if necessary in a closed vessel. The target product is obtained in free form as salts. For example, it is possible to obtain basic, neutral, mixed salts or hydrates of salt. PRI me R 1. 15 g 1-1i -. (Y, i d tt - - t Methylureido / -phenoxy / -2-hydroxy-3-aminopropane K1t t together with 150 ml of acetone for 3 hours. The solution is evaporated, the residue is dissolved and 2 g of palladium carbon () is added at a temperature of 20 C and rm at normal pressure. At the end of the hydrogen polishing stage, the catalyst is filtered off and the filtrate is dried to dryness. The residue is dissolved in BOOO ml of 2N hydrochloric acid, insoluble The hydrated parts are filtered off and extracted with methyl chloride. The aqueous phase is brought up by adding 2 cubic sodium hydroxide solution to an alkaline reaction and then extracted with methylene chloride. After evaporation of the solvent, - (K, n-dimethylureido) phenoxy (-2-hydroxy) is evaporated -3-isopropylaminopropane structural formula

ОНHE

/СНз/ SNZ

1one

(сНз),сштн yo-CHi-CH-cHjKdi (сНз), shtn yo-CHi-CH-cHjKdi

Claims (2)

плав щийс  после перекристаллизации из бензола при 138-139с. П р и м е р melting off after recrystallization from benzene at 138-139s. PRI me R 2. Аналогично примеру 1 можно также получить следующие соединени : -хлор-й-(ы, N -диметилуреидо))енокси -2-окси-3-изопропил-аминопропан с т.пл. 130 С; 1- 0-аллил- -(м ,Н -ди eтилуреидо ) 1фенокси -2-окси-3-изопропила1 {инопропан с т. пл. 110-112 С. -(м ,К -диметилуреидо)-фенокси -2-окси-З-изопропиламиноПропан , т. пл. 13О°С; -(N -метилуреидо)-фенокси1-2-окси-З-изопропиламинопропан , т. пл. 152-155°С, -(Ы -цикпог8ксипуреидо).фенокси -2-окси-3-иэопропиламштопропан , т. пл. 157-15 8°С. Формула изобретени  Способ получени  уреидофенокси-2-окси .3-аминопропанов общей формулы Л O-CHj-k-CHj-lCH-Bj л где R -водород, замещенный или незаме , алифатический остаток; «3 Эаме ««иь1Й или незамещенный алифатический остаток, или R, и R -вместе означают двухвалентный алифатический остаток, который может содержать гетероатом; R -алифатический или пиклоалифатический остаток и fjV- водород, низший алкил, низший алкенил, низший алкинил, циклоалкил, фенил-низший , алкил, низший алкоксил, фенил-низший алкенилоксил , низший алкинилоксил, галоид, а также замещенный низший алкил, фенокси-, трифторметил- или цианогруппа, причем уреидоостаток находитс  в мета-или пара- D положении по отношению к остатку, или юс солей, отличающийс  тем, что основание Шиффа структурной формулы П или III 0-CHj-CH CH°lf-Kj 5 ( 0-ai,-CH578861 . .ше значение, подвергают восстановлению, (.ljнапример, каталитическим гидрированием где 1, R., R; и имеют указанное выс последующим выделением целевого продук5 та в виде основани  или в виде соли.2. Analogously to Example 1, it is also possible to obtain the following compounds: -chloro-y (s, N-dimethylureido)) enoxy -2-hydroxy-3-isopropyl-aminopropane with m.p. 130 C; 1- 0-allyl- - (m, N-di-ethylureido) 1-phenoxy -2-hydroxy-3-isopropyl1 {alienpropane with m. Pl. 110-112 C. - (m, K-dimethylureido) -phenoxy -2-hydroxy-3-isopropylamino-propane, t. Pl. 13 ° C; - (N-methylureido) -phenoxy1-2-hydroxy-3-isopropylaminopropane, so pl. 152-155 ° C, - (S-cycpog-8xipureido). Phenoxy-2-hydroxy-3-isopropylamstropropane, m.p. 157-15 ° C The invention The method of obtaining ureidophenoxy-2-hydroxy. 3-aminopropanes of the general formula: L O-CHj-k-CHj-1CH-Bj where R is hydrogen, substituted or nezame, aliphatic residue; “3 Eame” “1bl” or unsubstituted aliphatic residue, or R, and R together stand for a bivalent aliphatic residue that may contain a heteroatom; R-aliphatic or picloaliphatic residue and fjV-hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, phenyl-lower, alkyl, lower alkoxy, phenyl-lower alkenyloxy, lower alkynyloxy, halogen, and also substituted lower alkyl, phenoxy, trifluoromethyl- or cyano, and the ureido residue is in the meta- or para- D position in relation to the residue, or yus salt, characterized in that the Schiff base of the structural formula P or III 0-CHj-CH CH? lf-Kj 5 (0- ai, -CH578861 .she value, is subjected to recovery, (.ljn example, catalytic hydr where 1, R., R; and have the above mentioned, followed by isolation of the desired product as a base or as a salt.
SU7201778355A 1970-01-08 1972-04-28 Method of preparing ureidophenoxy-2-oxy-3-aminopropanes SU578861A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH20470A CH554311A (en) 1970-01-08 1970-01-08 Cardioactive amines

Publications (1)

Publication Number Publication Date
SU578861A3 true SU578861A3 (en) 1977-10-30

Family

ID=4181620

Family Applications (6)

Application Number Title Priority Date Filing Date
SU1779647A SU475764A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes
SU1778353A SU474972A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy-2-oxy3 aminopropanes
SU1778352A SU450397A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes
SU1607281A SU420171A3 (en) 1970-01-08 1971-01-06 METHOD OF OBTAINING NONSATURATED AMINES
SU7201778543A SU563911A3 (en) 1970-01-08 1972-04-28 Method of producing ureidophenoxy-2-hydroxy-3-aminopropanes
SU7201778355A SU578861A3 (en) 1970-01-08 1972-04-28 Method of preparing ureidophenoxy-2-oxy-3-aminopropanes

Family Applications Before (5)

Application Number Title Priority Date Filing Date
SU1779647A SU475764A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes
SU1778353A SU474972A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy-2-oxy3 aminopropanes
SU1778352A SU450397A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes
SU1607281A SU420171A3 (en) 1970-01-08 1971-01-06 METHOD OF OBTAINING NONSATURATED AMINES
SU7201778543A SU563911A3 (en) 1970-01-08 1972-04-28 Method of producing ureidophenoxy-2-hydroxy-3-aminopropanes

Country Status (4)

Country Link
CH (1) CH554311A (en)
PL (2) PL94162B1 (en)
SU (6) SU475764A3 (en)
ZA (1) ZA708599B (en)

Also Published As

Publication number Publication date
SU474972A3 (en) 1975-06-25
CH554311A (en) 1974-09-30
SU450397A3 (en) 1974-11-15
ZA708599B (en) 1971-09-29
SU420171A3 (en) 1974-03-15
SU563911A3 (en) 1977-06-30
PL94154B1 (en) 1977-07-30
PL94162B1 (en) 1977-07-30
SU475764A3 (en) 1975-06-30

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SU420615A1 (en) METHOD FOR OBTAINING 2,4-DINITRO-3-AMINO-K-PHENYL HYDROXYLAMINE 12 A method is proposed for preparing 2,4-dinitro-3-amino-N-phenyl-hydroxylamine, which can be used in organic synthesis, in particular in the synthesis of aniline dyes , as well as in the synthesis of polymers. A method of producing phenylhydroxyl-silamine by reducing nitrobenzene with hydrogen in the presence of skeletal nickel, alkali metal sulphate salts and aniline is known. xylamine - a derivative of 2,4-dinitrobenzene, obium of formula 10, where R is an alkoxy group, is reacted with hydroxylamine and an alkali metal alcohol in an alcohol solution, followed by hydrolysis of the complex compound formed and the release of the desired product in its free form as known in a way. The reaction takes place at room temperature for 5-10 minutes with a yield of 80% according to the following scheme: