GB642159A - Improvements in or relating to the preparation of diphenyl ethers - Google Patents

Improvements in or relating to the preparation of diphenyl ethers

Info

Publication number
GB642159A
GB642159A GB2838047A GB2838047A GB642159A GB 642159 A GB642159 A GB 642159A GB 2838047 A GB2838047 A GB 2838047A GB 2838047 A GB2838047 A GB 2838047A GB 642159 A GB642159 A GB 642159A
Authority
GB
United Kingdom
Prior art keywords
dinitro
methoxyphenoxy
toluene
general formula
quaternary salt
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
GB2838047A
Inventor
Edward Teggin Borrows
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories Ltd
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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB2838047A priority Critical patent/GB642159A/en
Publication of GB642159A publication Critical patent/GB642159A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • 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
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin

Abstract

Diphenyl ethers of the general formula <FORM:0642159/IV (b)/1> are obtained by reacting a quaternary salt of the general formula <FORM:0642159/IV (b)/2> with a phenol of the general formula <FORM:0642159/IV (b)/3> wherein RN is a tertiary base which may be aliphatic, partly aromatic or one in which the nitrogen is part of a heterocyclic ring, e.g. pyridine, diethylaniline, the picolines, the dimethylpyridines and trimethylpyridines, R1 is one of the groups <FORM:0642159/IV (b)/4> or <FORM:0642159/IV (b)/5> where Z is an alkyl group containing not more than four carbon atoms and Y an acyl group normally used to protect an amino group, R11 is one of the following groups: H, -OH, alkyl, alkoxy, NO2, carbalkoxy, acyloxy and acylamino, and X is the anionic of an aromatic sulphonic acid, hydrochloric acid, hydrobromic acid or hydro-odic acid. The reaction may be carried out in solvents having a dielectric constant of less than 25, e.g. liquid sulphur dioxide, liquid ammonia, benzene or an excess of the tertiary organic base. The reaction may be effected by using the components of the quaternary salt without the isolation of the quaternary salt itself. Examples are given of the preparation of 3 : 5-dinitro-4-(41-hydroxy-or methoxy-phenoxy)-benzylhydantoin; ethyl-3 : 5 - dinitro - 4 - (41 - methoxyphenoxy) - dihydrocinnamate; 3 : 5-dinitro-4-(41-methoxyphenoxy), -4-phenoxy, -4-(41-methylphenoxy), - 4 - (41 - nitrophenoxy), - 4 - (41 - carbomethoxyphenoxy)-toluene; l-3 : 5-dinitro-4-(41-methoxyphenoxy or 41-acetoxyphenoxy) - N - acetylphenylalanine ethyl ester; 3 : 5-dinitro-4-(41-propionyloxyphenoxy)-toluene. Samples have been furnished under Sect. 2(5) of 3 : 5 - dinitro - 4 - (41 - acetamidophenoxy) - toluene; 3 : 5-dinitro-4-(41-acetamidophenoxy)-N-acetyl-dl or l-phenylalamine ethyl ester dl - 5 - 31 : 51 - dinitro - 41 - p - acetamidophenoxybenzyl)-hydantoin; and methyl-3 : 5-dinitro-4-(41-benzamidophenoxy)-benzoate.
GB2838047A 1947-10-23 1947-10-23 Improvements in or relating to the preparation of diphenyl ethers Expired GB642159A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2838047A GB642159A (en) 1947-10-23 1947-10-23 Improvements in or relating to the preparation of diphenyl ethers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2838047A GB642159A (en) 1947-10-23 1947-10-23 Improvements in or relating to the preparation of diphenyl ethers

Publications (1)

Publication Number Publication Date
GB642159A true GB642159A (en) 1950-08-30

Family

ID=10274735

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2838047A Expired GB642159A (en) 1947-10-23 1947-10-23 Improvements in or relating to the preparation of diphenyl ethers

Country Status (1)

Country Link
GB (1) GB642159A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5736576A (en) * 1996-06-04 1998-04-07 Octamer, Inc. Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US5922775A (en) * 1997-10-23 1999-07-13 Octamer, Inc. Method of treating malignant tumors with ketone thyroxine analogues having no significant hormonal activity
US6017958A (en) * 1996-06-04 2000-01-25 Octamer, Inc. Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US7189856B2 (en) 2001-12-28 2007-03-13 Gideon Shapiro Non-peptide somatostatin receptor ligands
US7199265B2 (en) * 2000-06-21 2007-04-03 Karo Bio Ab Thyroid receptor ligands, pharmaceutical compositions comprising them and their use in the treatment of disorders influenced by thyroid hormones

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5736576A (en) * 1996-06-04 1998-04-07 Octamer, Inc. Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US6017958A (en) * 1996-06-04 2000-01-25 Octamer, Inc. Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US5922775A (en) * 1997-10-23 1999-07-13 Octamer, Inc. Method of treating malignant tumors with ketone thyroxine analogues having no significant hormonal activity
US7199265B2 (en) * 2000-06-21 2007-04-03 Karo Bio Ab Thyroid receptor ligands, pharmaceutical compositions comprising them and their use in the treatment of disorders influenced by thyroid hormones
US7189856B2 (en) 2001-12-28 2007-03-13 Gideon Shapiro Non-peptide somatostatin receptor ligands

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