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SU1143745A1 - Method of obtaining derivatives of 3-(3-benzoxazolonyl) propionic acid - Google Patents

Method of obtaining derivatives of 3-(3-benzoxazolonyl) propionic acid Download PDF

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Publication number
SU1143745A1
SU1143745A1 SU833665476A SU3665476A SU1143745A1 SU 1143745 A1 SU1143745 A1 SU 1143745A1 SU 833665476 A SU833665476 A SU 833665476A SU 3665476 A SU3665476 A SU 3665476A SU 1143745 A1 SU1143745 A1 SU 1143745A1
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SU
USSR - Soviet Union
Prior art keywords
acid
reaction mixture
general formula
benzoxazolonyl
obtaining derivatives
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Application number
SU833665476A
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Russian (ru)
Inventor
Ромуальдас Стасисович Балтрушис
Зигмунтас-Ионас Генрикович Бересневичюс
Витаутас Юозович Мицкявичюс
Юсуф Хаджибекович Хапчаев
Любовь Леонидовна Миронова
Original Assignee
Каунасский Политехнический Институт Им.Антанаса Снечкуса
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Priority to SU833665476A priority Critical patent/SU1143745A1/en
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Publication of SU1143745A1 publication Critical patent/SU1143745A1/en

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 3-METHOD OF OBTAINING DERIVATIVES 3-

Description

Целью изобретени   вл етс  упроще-, Пример 3. Получение 3-(3ние технологии процесса, а также расширение ассортимента целевых продуктов .5$(0,5 моль) о-аминофенола, 43 гThe aim of the invention is to simplify, Example 3. Obtaining 3-(3 technology of the process, as well as expanding the range of target products. 5$(0.5 mol) o-aminophenol, 43 g

Поставленна  цель достигаетс  тем,(0,5 моль) кротоновой кислоты и 60 гThe set goal is achieved by (0.5 mol) of crotonic acid and 60 g

что согласно способу получени  сое-мочевины аналогично примеру 1 с выдинений общей формулы (I),за1шючак де-ходвм 79,3 г (72,1%). Характеристи .новую кислоту.that according to the method of obtaining soy urea similar to example 1 with the general formula (I) the yield was 79.3 g (72.1%). Characteristics.

бе« 0ксазолонн )-3-метилпропановойbe « 0xazolone )-3-methylpropane

киел9ты осуществл ют из 54,5 г ки и данные анализа приведены в таблице. Пример 4. Получение 3-(5хлор-3-бензоксазолонил )пропановой кислоты. Кип т т 1А,7 г (0,1 моль 4-хлор-2-аминоф нола,7,9 г (0,11 мол акриловой кислоты и 20 мл воды 2 ч, добавл ют 9,0 г (0,15 мол мочевины, 30 мл лед ной уксусной 454 кислоты и продолжают кип tить еще 3 ч. Затем в реакционную смесь добавл ют 30 мл концентрированной сол ной кислоты, перемешивают 3 мин и содержимое выливают в 300 мл воды. При охлаждении выделившуюс  3-(5хлор-3-бензоксазолонил )пропановую кислоту отфильтровывают. Выход 17,5 г (73%). Характеристики полученных соединений приведены в таблице.The extractions are carried out from 54.5 g of ki and the analytical data are given in the table. Example 4. Obtaining 3-(5-chloro-3-benzoxazolonyl)propanoic acid. Boil 1A, 7 g (0.1 mol) 4-chloro-2-aminofol, 7.9 g (0.11 mol) acrylic acid and 20 ml water for 2 h, add 9.0 g (0.15 mol) urea, 30 ml glacial acetic acid and continue boiling for another 3 h. Then add 30 ml concentrated hydrochloric acid to the reaction mixture, stir for 3 min and pour the contents into 300 ml water. Upon cooling, the separated 3-(5-chloro-3-benzoxazolonyl)propanoic acid is filtered off. Yield 17.5 g (73%). The characteristics of the obtained compounds are given in the table.

Claims (1)

СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 3-(3-БЕН30КСА30Л0НИП)ПР0ПАН0В0Й КИСЛОТЫ общей формулы METHOD FOR OBTAINING DERIVATIVES OF 3-(3-BEN30KSA30L0NIP)PR0PAN0V0Y ACID OF THE GENERAL FORMULA ΚιKI Ν- CHR2CHRjC00H где R<- атом водорода или хлора, R, и Rj- независимо один от другого атом водорода или метил, с использованием производного непредельной карбоновой кислоты и органического растворителя, отличающийс я тем, что, с целью упрощения технологии процесса и расширения ассор; тимента целевых продуктов, соответствующий о-аминофенол общей формулы где R, имеет указанные значения, подвергают взаимодействию с соответствующим производным непредельной; карбоновой кислоты общей формулы ! сн==б-(!оол ι I .N- CHR 2 CHRjC00H where R<- is a hydrogen or chlorine atom, R, and Rj- are independently of each other a hydrogen atom or methyl, using a derivative of an unsaturated carboxylic acid and an organic solvent, characterized in that, in order to simplify the process technology and expand the range of target products, the corresponding o-aminophenol of the general formula where R, has the indicated values, is subjected to interaction with the corresponding derivative of an unsaturated carboxylic acid of the general formula ! cн==6-(!оол ι I . Kg Ку где R2 и Rj имеют указанные значения, в среде уксусной кислоты в качестве органического растворителя и образующуюся соответствующую М-Со-оксифенил)-р-амийопропионовую кислоту непосредственно в · реакционной смеси подвергают взаимодействию с мочевиной с sO последующей обработкой реакционной смеси минеральной кислотой, процесс ведут при температуре кипения реакционной смеси.Kg Ku where R 2 and Rj have the indicated values, in a medium of acetic acid as an organic solvent and the resulting corresponding M-Co-oxyphenyl)-p-aminopropionic acid is directly reacted in the reaction mixture with urea with sO followed by treatment of the reaction mixture with a mineral acid, the process is carried out at the boiling temperature of the reaction mixture.
SU833665476A 1983-11-23 1983-11-23 Method of obtaining derivatives of 3-(3-benzoxazolonyl) propionic acid SU1143745A1 (en)

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SU833665476A SU1143745A1 (en) 1983-11-23 1983-11-23 Method of obtaining derivatives of 3-(3-benzoxazolonyl) propionic acid

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015091647A1 (en) 2013-12-19 2015-06-25 Glaxosmithkline Intellectual Property Development Limited 3-(5-chloro-2-oxobenzo[d]oxazol-3(2h)-yl)propanoic acid derivatives as kmo inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1. Алиев Н.А и др. Получение 3-бензоксазолрнил-/3- пропионитрилов. Узбекский химический журнал, 1979, Н 6, с. 51. 2. Lespagnol А. et al., 3-Benzoxazolinone alkanoic acids, Chlm. Ther, 1967, 2 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015091647A1 (en) 2013-12-19 2015-06-25 Glaxosmithkline Intellectual Property Development Limited 3-(5-chloro-2-oxobenzo[d]oxazol-3(2h)-yl)propanoic acid derivatives as kmo inhibitors
CN105829290A (en) * 2013-12-19 2016-08-03 葛兰素史密斯克莱知识产权发展有限公司 3-(5-Chloro-2-oxobenzo[d]oxazol-3-(2H)-yl)propionic acid derivatives as KMO inhibitors
KR20160098433A (en) * 2013-12-19 2016-08-18 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 3-(5-chloro-2-oxobenzo[d]oxazol-3(2h)-yl)propanoic acid derivatives as kmo inhibitors
AU2014368765B2 (en) * 2013-12-19 2017-12-07 Dr. Falk Pharma Gmbh 3-(5-chloro-2-oxobenzo(d)oxazol-3(2H)-yl)propanoic acid derivatives as KMO inhibitors
RU2693016C1 (en) * 2013-12-19 2019-07-01 Глэксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед Derivatives of 3-(5-chloro-2-oxobenzo[d]oxazol-3(2h)-yl)propanoic acid as kmo inhibitors
US11352334B2 (en) 2013-12-19 2022-06-07 The University Court Of The University Of Edinburgh 3-(5-chloro-2-oxobenzo[d]oxazol-3(2H)-yl) propanoic acid derivatives as KMO inhibitors
US12459906B2 (en) 2013-12-19 2025-11-04 Dr. Falk Pharma Gmbh 3-(5-chloro-2-oxobenzo[d]oxazol-3(2H)-yl) propanoic acid derivatives as KMO inhibitors

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