GB770410A - Bis(p-aminophenoxy) deriv?tives of aliphatic hydrocarbons - Google Patents

Bis(p-aminophenoxy) deriv?tives of aliphatic hydrocarbons

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Publication number
GB770410A
GB770410A GB2948853A GB2948853A GB770410A GB 770410 A GB770410 A GB 770410A GB 2948853 A GB2948853 A GB 2948853A GB 2948853 A GB2948853 A GB 2948853A GB 770410 A GB770410 A GB 770410A
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GB
United Kingdom
Prior art keywords
bis
group
ene
pentane
heptane
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
GB2948853A
Inventor
Clifford Gordon Raison
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 GB2948853A priority Critical patent/GB770410A/en
Publication of GB770410A publication Critical patent/GB770410A/en
Expired legal-status Critical Current

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Abstract

The invention comprises compounds of the general formula <FORM:0770410/IV(b)/1> and their acid addition salts in which R1 is an alkyl group of 2 to 4 carbon atoms substituted by at least one hydroxy group on a carbon atom other than that adjacent to the nitrogen, R2 is hydrogen, an alkyl group of 1 to 4 carbon atoms or an alkyl group of 2 to 4 carbon atoms substituted by at least one hydroxy group on a carbon atom other than that adjacent to the nitrogen atom and W is a polymethylene chain -(CH2)n- or -CH2-M-CH2-, in which n is an integer from 2 to 10 and m is an aliphatic chain of 2 to 8 carbon atoms having one or more double or triple bonds, such bonds not being adjacent in the case where more than one are present. The compounds may be prepared by (1) reacting an a : o -disubstituted compound of the formula X-W-X with a substituted phenyl compound of the formula <FORM:0770410/IV(b)/2> in which X and Y are radicals capable of reacting together to form an ether linkage and Z may be the group -NR1R2, when the latter is a tertiary amino group, or is a group capable of conversion to the group NR1R2, e.g. an acyl or nitroso group removed by hydrolysis or reduction respectively, and converting the group Z in the resulting bis-phenoxy compound as stated; (2) reacting the corresponding primary amine <FORM:0770410/IV(b)/3> with a compound R1B where B is a halogen or a sulphonic acid ester group, to give the corresponding secondary amines or the tertiary amines in which R2 is the same as R1; (3) where R1 and R2 are different, reacting the primary amine II first with a compound R1B and then with a compound R2B to give the tertiary amine; (4) reacting a primary amine of the formula II with an ethylene oxide derivative of the formula <FORM:0770410/IV(b)/4> to give products in which R1 or both R1 and R2 have the formula -CH2.CHOH.R3 (R3 being the remainder of the desired group) and (5) condensing a primary amine of the formula II with a halogenoalkyl chloroformate ester ClCOOR4Hal, in which R4 is an alkylene chain of 2 or 3 carbon atoms each of which may carry a methyl group as a substituent and Hal is a chlorine or bromine atom, followed by alkaline hydrolysis of the resulting intermediate cyclic compound. Examples describe the preparation of free bases or salts of compounds of the general formula I in which R1 is b -hydroxy ethyl, R2 is hydrogen and W is derived from propane, butane, pentane, hexane, heptane, octane, nonane, decane, but-2-ene, hex-3-ene and but-2-yne; R1 is b -hydroxyethyl, R2 is b -hydroxyethyl and W is derived from ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, but-2-ene, hex-3-ene, hept-3-ene, hexa-2 : 4-diene and but-2-yne; R1 is b -hydroxyethyl, R2 is methyl and W is derived from pentane, hexane, heptane, octane but-2-ene and but-2-yne, R1 is g -hydroxypropyl, R2 is hydrogen and W is derived from butane, pentane, hexane, heptane, and octane; R1 is b -hydroxyisopropyl, R2 is hydrogen and W is derived from hexane, heptane and octane; R1 is b -hydroxy-n-propyl, R2 is hydrogen and W is derived from but-2-ene; R1 is b -hydroxy-n-propyl, R2 is b -hydroxy-n-propyl and W is derived from hexane, heptane, octane, butane and pentane and R1 is b : g -dihydroxypropyl, R2 is hydrogen and W is derived from heptane. a : o - Bis (p - chloroalkoxycarbonamidophenoxy) alkanes and alkenes, used as intermediates in the preparation of compounds of the formula I, i.e. 1 : 5-bis-(p-b -chloroethoxycarbonamidophenoxy) pentane, 1 : 7-bis (p-g -chloropropoxycarbonamidophenoxy) heptane, 1 : 6-bis (p-b -chloroisopropoxycarbonamidophenoxy) hexane, 1 : 4 - bis - (p - b - chloroethoxycarbonamidophenoxy) but-2-ene, 1 : 4-bis (p - b - hydroxy - n - propylaminophenoxy) but-2-ene and 1 : 6-bis - (p - b - chloroethoxycarbonamidophenoxy) hex-3-ene are made by treating the corresponding 1 : 6-bis (p-aminophenoxy) alkane or alkene with the appropriate chloroalkyl chloroformate. 1 : 4 - Bis - (p - b - hydroxyethyl - N - nitrosoaminophenoxy) but-2-yne is made by treating p - b - hydroxyethyl - N - nitrosoaminophenol with 1 : 4-dichlorobut-2-yne. 1 : 5 - Bis - (p - [tetrahydro - oxazol - 2 - one - 3 - yl] phenoxy) pentane is obtained by heating 1 : 5 - bis - (p - chloroethoxycarbonamidophenoxy) pentane with potassium hydroxide in aqueous alcohol; further hydrolysis of this with aqueous sodium hydroxide gives 1 : 5-bis-(p-hydroxyethylaminophenoxy)pentane. Specifications 749,907, 749,923, 758,382 and 765,957 are referred to.
GB2948853A 1953-10-26 1953-10-26 Bis(p-aminophenoxy) deriv?tives of aliphatic hydrocarbons Expired GB770410A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2948853A GB770410A (en) 1953-10-26 1953-10-26 Bis(p-aminophenoxy) deriv?tives of aliphatic hydrocarbons

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2948853A GB770410A (en) 1953-10-26 1953-10-26 Bis(p-aminophenoxy) deriv?tives of aliphatic hydrocarbons

Publications (1)

Publication Number Publication Date
GB770410A true GB770410A (en) 1957-03-20

Family

ID=10292340

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2948853A Expired GB770410A (en) 1953-10-26 1953-10-26 Bis(p-aminophenoxy) deriv?tives of aliphatic hydrocarbons

Country Status (1)

Country Link
GB (1) GB770410A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161474A (en) 1977-11-25 1979-07-17 Monsanto Company Bis-(alkylaminophenoxy)alkanes as antidegradants for rubber

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161474A (en) 1977-11-25 1979-07-17 Monsanto Company Bis-(alkylaminophenoxy)alkanes as antidegradants for rubber

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