GB749907A - Improvements in bis-(p-aminophenoxy) alkane derivatives - Google Patents
Improvements in bis-(p-aminophenoxy) alkane derivativesInfo
- Publication number
- GB749907A GB749907A GB3080552A GB3080552A GB749907A GB 749907 A GB749907 A GB 749907A GB 3080552 A GB3080552 A GB 3080552A GB 3080552 A GB3080552 A GB 3080552A GB 749907 A GB749907 A GB 749907A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- pentane
- group
- nitroso
- hexane
- 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
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0749907/IV(a)/1> and their acid addition salts where n is an integer from 3 to 10 and R is an alkyl or alkenyl radical of 1 to 5 carbon atoms. The compounds are made by the following methods. (1) A compound of the formula <FORM:0749907/IV(a)/2> where Z is a substituent which is convertible into a secondary amino group is converted by known methods for introducing a secondary amino group into an aromatic compound; e.g. a protecting group W is removed from a group RWN- such as by hydrolysis of an acyl, toluene-p-sulphonyl, or alkoxycarbonyl group, or removal of a nitroso group by reduction or by reaction with urea and acid or of a benzyl group by hydrogenation; a benzylidene amino group is treated with an alkylating agent containing the group R and the product is hydrolysed; a carboxyalkylamino group is decarboxylated; a primary amino group is alkylated either directly or by reductive alkylation with an aldehyde; an aliphatic acyl amido group is reduced for example by lithium aluminium hydride; a group WHN-, where W is a protecting group such as an acyl, e.g. acetyl, formyl or toluene-p-sulphonyl, group is alkylated and the protecting group W is removed or a compound in which Z is a halogen atom, e.g. chlorine, is aminated. (2) An a :o - disubstituted alkane of the general formula X-(CH2)n -X is reacted with a disubstituted benzene of the formula <FORM:0749907/IV(a)/3> where X and Y are groups capable of reacting together to form an ether linkage, e.g. Y is a hydroxy group and X is a halogen atom such as bromine or chlorine or a mesyl or tosyl group. (3) A monophenoxy compound of the formula <FORM:0749907/IV(a)/4> is reacted with a disubstituted benzene of the formula given under (2) above. The compounds are used in the treatment of schistosomiasis. Examples describe the use of the above methods in the preparation of a :o -bis-(p - methylaminophenoxy), - propane, - butane, - pentane, - hexane, - heptane, - octane, - nonane and - decane; a :o - bis-(p - ethylaminophenoxy), - propane, - pentane, - hexane, - heptane, - octane and - nonane; a :o - bis-(p - n - propylaminophenoxy), - pentane, - hexane, - heptane, -octane and - nonane; a :o - bis - (isopropylaminophenoxy), - hexane, - heptane and - octane; a :o - bis - p( - n - and isobutylaminophenoxy), -hexanes, -heptanes and octanes; a :o - bis - (p - n - amylaminophenoxy), -hexane, -heptane and -octane and a :o - bis - (p - allylaminophenoxy), - hexane, -heptane and -octane. Some of these products are isolated in the form of the acid addition salts. Acid amides.-p - Hydroxyacetethylanilide prepared from acetic anhydride and p-ethylaminophenol is reacted with 1:6-dibromohexane to give 1:6 - bis - (p acetethylamino phenoxy) hexane. p - Hydroxyacet - n - propylanilide, p - hydroxyacet - n - butylanilide, p-hydroxyacet - n - amylanilide, p - hydroxyacetallylanilide, and p - hydroxyacet - isobutylanilide are similarly prepared and reacted with 1:6-dibromohexane or with other a :o -dibromoalkanes. 1:5 - Bis - (p - formamidophenoxy) pentane is made by heating 1:5-bis-(p-aminophenoxy) pentane with formic acid. 6-(p-Acetmethylamidophenoxy) hexyl bromide is made by the reaction of p-acetmethylamidophenol with an excess of 1:6-dibromohexane. p-Ethoxycarbonmethylamidophenol is prepared by the reaction of ethyl chloroformate and p-methylaminophenol sulphate in the presence of sodium acetate and is subsequently condensed with 1:5-dibromopentane. Sulphonamides.-p - (Toluene - p - sulphonmethylamido) phenol is heated with 1:5 - dibromopentane to give 1:5-bis-(p-(toluene-p-sulphonmethylamido) phenoxy) pentane. The same product is obtained by reaction of toluene-p-sulphonyl chloride with 1:5-bis-(p-aminophenoxy) pentane. 1:5 - Bis - (p - benzylideneaminophenoxy) pentane is made by reaction of benzaldehyde with 1:5-bis-(p-aminophenoxy) pentane. 1:5 - Bis - (p - benzylaminophenoxy) pentane is made by catalytic reduction of 1:5-bis-(p-benzylideneamino phenoxy) pentane. Reaction of the product with n-propyl iodide gives 1:5-bis - (p - benzyl - n - propylaminophenoxy) pentane. 1:5 - Bis - (p - carbethoxymethylaminophenoxy) pentane is made by reacting 1:5-bis-(p-aminophenoxy) pentane with ethyl chloroacetate in the presence of sodium acetate. Hydrolysis of this ester gives bis-(p-carboxymethylaminophenoxy) pentane. Nitroso compounds.-N-Nitroso-p-isopropylaminophenol, N - nitroso - p - ethylaminophenol, N - nitroso - p - methylaminophenol and N-nitroso - p - n - propylaminophenol are made by the action of nitrous acid on the corresponding alkylaminophenols. These compounds are reacted with a :o -dibromoalkanes to give inter alia: N:N1 - dinitroso - 1:6 - bis - (p - methylaminophenoxy) hexane and N:N1 - dinitroso-1:5 - bis - (p - methylaminophenoxy) pentane. The former compound is also prepared by the reaction of N-nitroso 6-(p-methylaminophenoxy) hexyl bromide with N-nitroso-p-methylaminophenol. Specifications 722,980, [Group III], and 749,923 are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3080552A GB749907A (en) | 1952-12-04 | 1952-12-04 | Improvements in bis-(p-aminophenoxy) alkane derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3080552A GB749907A (en) | 1952-12-04 | 1952-12-04 | Improvements in bis-(p-aminophenoxy) alkane derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB749907A true GB749907A (en) | 1956-06-06 |
Family
ID=10313408
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3080552A Expired GB749907A (en) | 1952-12-04 | 1952-12-04 | Improvements in bis-(p-aminophenoxy) alkane derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB749907A (en) |
Cited By (5)
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 |
JPS4897828A (en) * | 1972-02-25 | 1973-12-13 | ||
US3862226A (en) * | 1972-02-28 | 1975-01-21 | Burroughs Wellcome Co | Bis-{8 beta-(4-N,N-diacetylaminophenoxy)ethyl{9 ether |
DE2850995A1 (en) * | 1977-11-25 | 1979-05-31 | Monsanto Co | BIS-ALKYLAMINOPHENOXYALKANES AS ANTIDEGRADATING AGENTS IN SERVICE RUBBER |
WO1984000886A1 (en) * | 1982-08-27 | 1984-03-15 | Gerald M Rosen | N-alkyl-4'-hydroxyacetanilides, pharmaceutical compositions comprising them and their use |
-
1952
- 1952-12-04 GB GB3080552A patent/GB749907A/en not_active Expired
Cited By (7)
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 |
JPS4897828A (en) * | 1972-02-25 | 1973-12-13 | ||
US3862226A (en) * | 1972-02-28 | 1975-01-21 | Burroughs Wellcome Co | Bis-{8 beta-(4-N,N-diacetylaminophenoxy)ethyl{9 ether |
DE2850995A1 (en) * | 1977-11-25 | 1979-05-31 | Monsanto Co | BIS-ALKYLAMINOPHENOXYALKANES AS ANTIDEGRADATING AGENTS IN SERVICE RUBBER |
US4161474A (en) | 1977-11-25 | 1979-07-17 | Monsanto Company | Bis-(alkylaminophenoxy)alkanes as antidegradants for rubber |
FR2416917A1 (en) * | 1977-11-25 | 1979-09-07 | Monsanto Co | VULCANIZABLE DIENIC RUBBER COMPOSITIONS CONTAINING BIS-ALKYLAMINOPHENOXYALCANES AS ANTIDEGRADANT PRODUCTS FOR RUBBER |
WO1984000886A1 (en) * | 1982-08-27 | 1984-03-15 | Gerald M Rosen | N-alkyl-4'-hydroxyacetanilides, pharmaceutical compositions comprising them and their use |
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