GB756937A - New derivatives of phenthiazine and their method of preparation - Google Patents
New derivatives of phenthiazine and their method of preparationInfo
- Publication number
- GB756937A GB756937A GB1008753A GB1008753A GB756937A GB 756937 A GB756937 A GB 756937A GB 1008753 A GB1008753 A GB 1008753A GB 1008753 A GB1008753 A GB 1008753A GB 756937 A GB756937 A GB 756937A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aza
- dichloride
- diazanium
- chlorophenthiazinyl
- prepared
- 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 phenthiazines containing the cation <FORM:0756937/IV(a)/1> wherein A is a saturated straight or branched chain divalent aliphatic hydrocarbon group comprising 2 or 3 carbon atoms, n is 2 or 3, R is methyl or ethyl, R1 is hydrogen, an alkyl radical comprising 1 to 4 carbon atoms, or a benzyl or acyl group, and Y is a hydrogen or halogen atom or a methyl, methoxy or phenoxy group. The compounds are prepared (1) by heating an amine <FORM:0756937/IV(a)/2> with at least two molar proportions of a dialkylaminoalkylphenthiazine <FORM:0756937/IV(a)/3> to a temperature of 50 DEG -110 DEG C. in a polar solvent; (2) by heating under conditions as in (1) a compound of formula <FORM:0756937/IV(a)/4> with at least one molar (preferably an equimolar) proportion of a dialkylaminoalkylphenthiazine as in (1); (3) by deacylating the reaction products from methods (1) and (2) when R1 is acyl; (4) by reducing the reaction products from methods (1) and (2) when R1 is acyl, thereby converting R1 to an alkyl or benzyl group; and (5) by converting the halogen anion in the reaction products of methods (1) to (4) to an anion of another acid by treatment with an alkali metal or silver salt of such acid. The polar solvent mediums specified are alcohols, nitrobenzene or dimethylformamide, and preferably ethanol employed under reflux conditions. The examples describe the preparation of 1 : 11-di-(31-chlorophenthiazinyl - 101) - 3 : 3 : 9 : 9 - tetramethyl-6 - ethyl - 6 - aza - 3 : 9 - diazanium - undecane dichloride; 1 : 11-di-(31-chloro- and 31-methylphenthiazinyl - 101) - 3 : 3 : 9 : 9 - tetramethyl - 6 - aza - 3 : 9 - diazanium - undecane dichloride hydrochloride; 1 : 11 - di - (31-chlorophenthiazinyl - 101) - 3 : 3 : 9 : 9 - tetramethyl - 6 - aza - 6 - formyl - 3 : 9 - diazanium-undecane dichloride; 1 : 11 - di - (phenthiazinyl - 101, 31 - chloro -, 31 - methyl -, 31-methoxy- and 31-phenoxyphenthiazinyl-101)-3 : 3 : 6 : 9 : 9 - pentamethyl - 6 - aza - 3 : 9-diazanium-undecane dichloride (the picrate, diperchlorate, bis-methanesulphonate, bis-paratoluenesulphonate and bis-benzoate of the 31-chloro derivative are also described); 1 : 11-di - (phenthiazinyl - 101 and 31 - chlorophenthiazinyl - 101) - 3 : 3 : 9 : 9 - tetramethyl-6 - butyl - 6 - aza - 3 : 9 - diazanium - undecane dichloride and di-iodide; 1 : 13-di-(31-chlorophenthiazinyl - 101) - 4 : 4 : 10 : 10 - tetramethyl - 7 - benzyl - 7 - aza - 4 : 10 - diazaniumtridecane dichloride; 1 : 13-di-(31-chlorophenthiazinyl - 101) - 7 - methyl - 4 : 4 : 10 : 10-tetraethyl - 7 - aza - 4 : 10 - diazanium - tridecane dichloride; 1 : 13-di-(31-chlorophenthiazinyl - 101) - 3 : 3 : 7 : 11 : 11 - pentamethyl - 7 - aza - 3 : 11 - diazanium - tridecane dichloride; 1 : 13 - di - (phenthiazinyl - 101,31-methyl-, 31-methoxy- and 31-chlorophenthiazinyl - 101) - 4 : 4 : 7 : 10 : 10 - pentamethyl-7 - aza - 4 : 10 - diazanium - tridecane dichloride; and 1 : 15-di-(31-chlorophenthiazinyl - 101) - 4 : 4 : 8 : 12 : 12 - pentamethyl-8 - aza - 4 : 12 - diazanium - pentadecane dichloride. The amine starting materials used in method (2) are prepared from the reactants specified in method (1), using the same solvents but employing temperatures below 50 DEG C. 2 : 21 - Dichlorotriethylamine, N : N - di-(2 - chloroethyl) - benzylamine, N : N - di - (3-chloropropyl) - methylamine and N : N - di-(2-chloroethyl)-formamide are prepared by reacting thionyl chloride with N-ethyldiethanolamine, N-benzyldiethanolamine, di-(3-hydroxypropyl)-methylamine and N : N-di-(2-hydroxyethyl)-formamide respectively. N-Ethyldiethanolamine is prepared by reacting ethylamine with ethylene oxide. N-Benzyldiethanolamine is prepared by reacting benzyl chloride with diethanolamine. Di-(3-hydroxypropyl)-methylamine is prepared by lithium aluminium hydride reduction of di - (2 - methoxycarbonylethyl) - methylamine. N : N - Di - (2 - hydroxyethyl) - formamide is prepared by prolonged boiling of diethanolamine with excess of formamide.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1008753A GB756937A (en) | 1953-04-13 | 1953-04-13 | New derivatives of phenthiazine and their method of preparation |
ES0214693A ES214693A1 (en) | 1953-04-13 | 1954-04-12 | New derivatives of phenthiazine and their method of preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1008753A GB756937A (en) | 1953-04-13 | 1953-04-13 | New derivatives of phenthiazine and their method of preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
GB756937A true GB756937A (en) | 1956-09-12 |
Family
ID=9961227
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1008753A Expired GB756937A (en) | 1953-04-13 | 1953-04-13 | New derivatives of phenthiazine and their method of preparation |
Country Status (2)
Country | Link |
---|---|
ES (1) | ES214693A1 (en) |
GB (1) | GB756937A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2918464A (en) * | 1956-04-06 | 1959-12-22 | Burroughs Wellcome Co | Diquaternary ammonium compounds and the manufacture thereof |
-
1953
- 1953-04-13 GB GB1008753A patent/GB756937A/en not_active Expired
-
1954
- 1954-04-12 ES ES0214693A patent/ES214693A1/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2918464A (en) * | 1956-04-06 | 1959-12-22 | Burroughs Wellcome Co | Diquaternary ammonium compounds and the manufacture thereof |
Also Published As
Publication number | Publication date |
---|---|
ES214693A1 (en) | 1955-06-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR830007644A (en) | Process for preparing carbostyryl compound | |
ES521032A0 (en) | PROCEDURE FOR PREPARING PYRROLICIDINIC DERIVATIVES 8 SUBSTITUTED. | |
GB756937A (en) | New derivatives of phenthiazine and their method of preparation | |
ES421068A1 (en) | Procedure for the preparation of new 2-phenylamine-substitute imidazolines. (Machine-translation by Google Translate, not legally binding) | |
GB1124246A (en) | Novel quinazoline derivatives and a process for the preparation thereof | |
GB840384A (en) | Improvements in or relating to hemicyanine dyestuffs | |
ES472009A1 (en) | Copper complexes of N-pyrazole, N-imidazole and N-triazole acetanilides, their preparation and their use as fungicides. | |
GB777544A (en) | Water soluble organic copper compounds and a process for their production | |
GB843752A (en) | Novel morphinane derivatives and a process for the manufacture thereof | |
GB714230A (en) | Pyridine compounds and process for the manufacture thereof | |
US3127447A (en) | Methylnaphthalene derivatives | |
GB1070139A (en) | Novel imidazothiazole derivatives and a process for preparation thereof | |
GB845486A (en) | Improvements in or relating to 2-diarylalkyl-3,4,5,6-tetrahydropyrimidines | |
GB748358A (en) | Improvements in or relating to pyrimidines | |
ES219460A1 (en) | New phenthiazine derivatives and processes for their preparation | |
GB744281A (en) | Improvements in and relating to pyridine derivatives and the manufacture thereof | |
GB786384A (en) | Basic alkoxyalkyl esters of phenothiazine-10-carboxylic acid and process for preparing same | |
GB843908A (en) | Novel morphinan derivatives and the manufacture thereof | |
GB742340A (en) | Improvements in or relating to diaminoadiponitriles | |
GB852971A (en) | New n-substituted camphidine derivatives and processes for their preparation | |
GB717213A (en) | Method of preparing anaesthetics | |
GB605710A (en) | Improvements in or relating to substituted diamines | |
GB712461A (en) | New guanidine derivatives | |
GB793010A (en) | Substituted piperidine 4-carboxylic esters | |
GB867930A (en) | Substituted pyridones |