GB749923A - Bis-(ú­-aminophenoxy) alkanes - Google Patents

Bis-(ú­-aminophenoxy) alkanes

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Publication number
GB749923A
GB749923A GB56354A GB56354A GB749923A GB 749923 A GB749923 A GB 749923A GB 56354 A GB56354 A GB 56354A GB 56354 A GB56354 A GB 56354A GB 749923 A GB749923 A GB 749923A
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GB
United Kingdom
Prior art keywords
bis
group
converted
hexane
treated
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
GB56354A
Inventor
Albert Gordon Caldwell
John Henry Gorvin
Clifford Gordon Raison
Eric Walton
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB56354A priority Critical patent/GB749923A/en
Publication of GB749923A publication Critical patent/GB749923A/en
Expired legal-status Critical Current

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Abstract

The invention comprises compounds of the formula <FORM:0749923/IV(a)/1> and acid addition salts thereof where n is an integer from 4 to 9, more preferably from 6 to 9. They are made by the following methods. (1) A compound of the formula <FORM:0749923/IV(a)/2> where Z is a group convertible to an amino group is so converted, e.g. a group -NHR where R is a protecting group is converted by removing the group R, e.g. an acyl group such as acetyl, alkoxycarbonyl, toluene-p-sulphonyl, is removed by hydrolysis; a phthalimido group is converted by hydrolysis; a halogen such as bromine is converted by amination; a nitroso, nitro or azo group is converted by reduction; an aldimino group is converted by hydrolysis or reduction; a carboxylic acid group is converted by Curtius reaction via the acid azide which by treatment with an alcohol followed by hydrolysis gives in turn an alkoxy carbonamido group and the desired amino group; a carboxylic amide group is converted by the Hofmann reaction or an isocyanate or urea group is converted by hydrolysis. (2) A disubstituted phenoxy alkane of the formula X(CH2)nX is reacted with a compound of the formula <FORM:0749923/IV(a)/3> where X and Y are groups capable of reacting together to form an ether linkage, and the group Z is subsequently converted into an amino group, for example Y may be hydroxy and an X may be halogen such as bromine or may be an alkanesulphonyl or aranesulphonyl group such as a methyl sulphonyl or toluene-b -sulphonyl group. The products may be used in the treatment of schistosomiasis. In examples (1) p-nitrophenol is treated with 1:6-dibromo hexane and the resulting 1:6-bis-(p-nitrophenoxy) hexane is reduced to 1:6-bis-(p-aminophenoxy) hexane; (2) 1:6-bis-(p-nitrophenoxy) hexane is reduced in glacial acetic acid to give 1:6-bis-(p-acetamidophenoxy) hexane which is hydrolysed to the product of (1); (3) p-hydroxybenzanilide is treated with 1:5-dibromopentane and the resulting 1:5-bis-(p-benzamidophenoxy) pentane is hydrolysed to 1:5-bis-(p-aminophenoxy) pentane; (4) p-ethoxycarbonamidophenol, obtained by the action of ethyl chloroformate on p-aminophenol, is treated with 1:6-dibromohexane and the product is hydrolysed to give the product of (1); (5) benzylideneaminophenol is treated with 1:4-dibromobutane and the resulting 1:4-bis - (p - benzylideneaminophenoxy) butane is hydrolysed or reduced to 1:4-bis-(p-aminophenoxy) butane; (6) p-benzeneazophenol is treated with 1:6-dibromohexane and the resulting 1:6-bis-(p-benzeneazophenoxy) hexane benzoate is treated with 1:5-dibromopentane to give 1:5-bis-(p-ethoxycarbonylphenoxy) pentane, reaction of this with hydrazone gives the corresponding bis-hydrazide which is converted to the corresponding acid azide by treatment with sodium nitrite, the azide is refluxed with alcohol to give 1:5-bis-(p-ethoxycarbonylaminophenoxy) pentane and hydrolysis of this gives the product of (2); (8) p-phthalimidophenol is treated with 1:6-dibromohexane and the resulting 1:6-bis-(p-phthalimidophenoxy) hexane is hydrolysed to give the product of (1); (9) 1:6-bis-(p-bromophenoxy) hexane is aminated by treating with a mixture of liquid ammonia and ethyl alcohol in the presence of copper bronze at an elevated temperature and pressure to give the product of (1) and (10) p-hydroxyacetanilide is treated with 1:5-dibromopentane and the product is hydrolysed to give the product of (2). The method of 10 is also used to prepare the full range of a :o -bis-(p-aminophenoxy) alkanes from butane to nonane.
GB56354A 1953-01-14 1953-01-14 Bis-(ú­-aminophenoxy) alkanes Expired GB749923A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB56354A GB749923A (en) 1953-01-14 1953-01-14 Bis-(ú­-aminophenoxy) alkanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB56354A GB749923A (en) 1953-01-14 1953-01-14 Bis-(ú­-aminophenoxy) alkanes

Publications (1)

Publication Number Publication Date
GB749923A true GB749923A (en) 1956-06-06

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ID=9706567

Family Applications (1)

Application Number Title Priority Date Filing Date
GB56354A Expired GB749923A (en) 1953-01-14 1953-01-14 Bis-(ú­-aminophenoxy) alkanes

Country Status (1)

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GB (1) GB749923A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1144290B (en) * 1958-06-24 1963-02-28 May & Baker Ltd Process for the production of new substituted aminophenols
JPS63122640A (en) * 1986-11-11 1988-05-26 Nippon Mining Co Ltd Novel compound and liquid crystal composition containing said compound
WO2005113487A2 (en) * 2004-05-14 2005-12-01 Sawyer Kenneth I Polyurea compositions and compounds for the preparation thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1144290B (en) * 1958-06-24 1963-02-28 May & Baker Ltd Process for the production of new substituted aminophenols
JPS63122640A (en) * 1986-11-11 1988-05-26 Nippon Mining Co Ltd Novel compound and liquid crystal composition containing said compound
JPH0759527B2 (en) 1986-11-11 1995-06-28 株式会社ジャパンエナジー Novel compound and liquid crystal composition containing the same
WO2005113487A2 (en) * 2004-05-14 2005-12-01 Sawyer Kenneth I Polyurea compositions and compounds for the preparation thereof
WO2005113487A3 (en) * 2004-05-14 2006-06-01 Kenneth I Sawyer Polyurea compositions and compounds for the preparation thereof

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