GB1506913A - Process for the preparation of 2-phenylamino-2-imidazoline derivatives - Google Patents

Process for the preparation of 2-phenylamino-2-imidazoline derivatives

Info

Publication number
GB1506913A
GB1506913A GB1130575A GB1130575A GB1506913A GB 1506913 A GB1506913 A GB 1506913A GB 1130575 A GB1130575 A GB 1130575A GB 1130575 A GB1130575 A GB 1130575A GB 1506913 A GB1506913 A GB 1506913A
Authority
GB
United Kingdom
Prior art keywords
formula
hydrogen
compound
benzoyl
phosphorus oxychloride
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB1130575A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Patheon Austria GmbH and Co KG
Original Assignee
Chemie Linz AG
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 Chemie Linz AG filed Critical Chemie Linz AG
Priority to GB1130575A priority Critical patent/GB1506913A/en
Publication of GB1506913A publication Critical patent/GB1506913A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1506913 Process for preparation of 2-phenylamino - 2 - imidazoline derivatives CHEMIE LINZ AG 18 March 1975 11305/75 Heading C2C The invention comprises a process for preparing compounds of the Formula Ia or Ib in which each of R 1 , R 2 and R 3 are independently hydrogen, halogen, C 1-4 -alkyl, C 1-4 alkoxy or nitro, with the proviso that at least one of R 1 , R 2 and R 3 is not hydrogen, and R 4 is hydrogen or R 5 , wherein R 5 is benzoyl which is optionally substituted by methyl or ethyl, or a salt thereof in which an aniline derivative of the Formula II is reacted with a 1-benzoyl-imidazolidin-2-one of the Formula III in the presence of at least 2 mols of phosphorus oxychloride per mol of compound II, at a temperature from room temperature to the boiling point of phosphorus oxychloride at normal pressure, and subjecting the intermediate obtained, after removing excess phosphorus oxychloride, to mild hydrolysis, after which, if desired, in the resulting compound of the Formula Ia or Ib in which R 4 is R 5 , the benzoyl group is split off by treatment with an alcohol, acid or alkaline compound to yield a compound of the Formula Ia or Ib in which R 4 is hydrogen, and isolating the product, where R 4 is H or R 5 , as a free base or an acid addition salt. The mild hydrolysis and removal of the benzoyl group at R 4 may be effected in a single step by treatment with one of the splitting agents. Some of the compounds of the Formulae Ia and Ib are claimed per se in Specification 1,506,914.
GB1130575A 1975-03-18 1975-03-18 Process for the preparation of 2-phenylamino-2-imidazoline derivatives Expired GB1506913A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1130575A GB1506913A (en) 1975-03-18 1975-03-18 Process for the preparation of 2-phenylamino-2-imidazoline derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1130575A GB1506913A (en) 1975-03-18 1975-03-18 Process for the preparation of 2-phenylamino-2-imidazoline derivatives

Publications (1)

Publication Number Publication Date
GB1506913A true GB1506913A (en) 1978-04-12

Family

ID=9983808

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1130575A Expired GB1506913A (en) 1975-03-18 1975-03-18 Process for the preparation of 2-phenylamino-2-imidazoline derivatives

Country Status (1)

Country Link
GB (1) GB1506913A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3518604A1 (en) 1984-05-23 1985-11-28 Egyt Gyógyszervegyészeti Gyár, Budapest METHOD FOR THE PRODUCTION OF 2- (PHENYLIMINO) -IMIDAZOLIDINE DERIVATIVES

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3518604A1 (en) 1984-05-23 1985-11-28 Egyt Gyógyszervegyészeti Gyár, Budapest METHOD FOR THE PRODUCTION OF 2- (PHENYLIMINO) -IMIDAZOLIDINE DERIVATIVES

Similar Documents

Publication Publication Date Title
GB1450250A (en) Process for the manufacture of 2-arylamino-2-imidazoline derivatives and their salts
FI873380A (en) FOERFARANDE FOER FRAMSTAELLNING AV KINOLINKARBOXYLSYROR.
WO1987007605A1 (en) Novel biphenyl derivatives, process for their preparation, and their use
DK682288D0 (en) METHOD OF PREPARING QUINOLINCARBOXYL ACID
GB1506913A (en) Process for the preparation of 2-phenylamino-2-imidazoline derivatives
GB1505020A (en) Substituted 2-phenylimino-thiazolines a process for their preparation and their use as ectoparasiticides
Patai et al. 137. Tritylation and detritylation of active methylene compounds. Part I. Tritylation by various triarylmethanols
US3665005A (en) Process for preparing 4-hydroxy-6,7-substituted-3-carboalkoxyquinolines
ES8306161A1 (en) Novel nitrosourea derivative, process for preparing same and therapeutic composition containing said derivate.
MX173989B (en) PROCEDURE FOR THE PREPARATION OF GLUTARIC ACID DERIVATIVES
EP0134245A4 (en) Process for preparing 3-chloro-1-formyl-4-phenyl-pyrroles.
GB1414825A (en) Process for the preparation of substituted chloroacetanilides
JPS51133243A (en) Process for preparing phthalamic acid ester derivatives
JPS57126427A (en) Preparation of 1-substituted-azulene derivative
JPS5785352A (en) Preparation of n-arylamidinecarboxylic acid
JPS5721387A (en) Preparation of oxazolidinone derivative
SE8303565L (en) PROCEDURE FOR THE PREPARATION OF 1-ALKYL OR 1,4-DIALKYL-1H-PYRROL-2-ETHYAC ACID ESTERS
JPS5643271A (en) Production of 4-benzoyl-5-hydroxypyrazole
JPS55151547A (en) Production of guanidinocapronic ester
GB1341072A (en) Aryliminothiazolidines processes for their preparation and their use as acaricides
JPS5721386A (en) Preparation of oxazolidinone derivative
JPS56123972A (en) Preparation of 1,3-dialkyl-4-benzoyl-5-hydroxypyrazole compound
GB799272A (en) Production of intermediates for the synthesis of reserpine and analogous compounds
GB1282894A (en) Process for the manufacture of aminopyrazolones
JPS5564575A (en) Preparation of 3-acyl-5-fluorouracil

Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee