GB789430A - Derivatives of amino-thiochromanones and amino-thiochromones - Google Patents
Derivatives of amino-thiochromanones and amino-thiochromonesInfo
- Publication number
- GB789430A GB789430A GB13238/56A GB1323856A GB789430A GB 789430 A GB789430 A GB 789430A GB 13238/56 A GB13238/56 A GB 13238/56A GB 1323856 A GB1323856 A GB 1323856A GB 789430 A GB789430 A GB 789430A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- amino
- dimethyl
- diethylaminoethylamino
- methylthiochromone
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 5-substituted-8-methyl-thiochromanones and thiochromones of the general formul : <FORM:0789430/IV (b)/1> wherein X represents an aliphatic chain, Y is a tertiary amino group, and the molecule can be substituted in the 2- or 3-position, e.g. by alkyl, alkoxy, aryl, halogen-aryl and alkoxy-aryl; and processes for their preparation: (a) by reacting a 5-aminothiochromanone or thiochromone with a reactive ester of an amino alcohol or a salt thereof, preferably in the presence of a dehydrating agent; (b) by reacting a 5-halogen-thiochromanone or thiochromone with an aliphatic diamine in which at least one amino group contains a free hydrogen atom; (c) by condensing a 5-hydroxy-thiochromanone or thiochromone or an ether thereof with a diamine as in (b); (d) by reacting an amino-thiochromanone or thiochromone with an alkylene oxide or alkylene halohydrin, treating the corresponding hydroxyalkyl compound with phosphorus oxychloride and reacting the resultant halide with an amine; (e) by addition of a 5-aminothiochromanone or thiochromone to acrylonitrile and subsequent hydrogenation of the cyano group to an aminomethyl group; (f) by condensation of a b -(5-aminophenylmercapto) fatty acid ester with a reactive ester of an amino alcohol and cyclization of the resulting, basically alkylated compound with a dehydrating agent. In examples: (1) sodium pyrosulphite is added to a solution of KI, 4-nitrotoluene - 2 - sulphochloride and HCl in aqueous dioxane, giving 2,21-dimethyl-5,51-dinitrodiphenyldisulphide (A), which is suspended in alcohol and treated with sodium sulphide in NaOH and then with chloropropionic acid to yield b - (2 - methyl - 5 - nitrophenylmercapto)-propionic acid; ferrous sulphate reduction yields the 5-amino derivative, which after cyclization with H2SO4 to 5-amino-8-methylthiochromanone is reacted with diethylaminoethyl chloride to give 5-diethylaminoethylamino - 8 - methylthiochromanone; (2) treatment of A as in (1) using b -chlorobutyric acid gives b - (2 - methyl - 5 - nitrophenylmercapto) butyric acid, the 5-amino derivative, 2,8-dimethyl - 5 - aminothiochromanone, and finally 2,8 - dimethyl - 5 - diethylaminoethylaminothiochromanone; (3) as in (2) using b -chlorovaleric acid gives 2-ethyl-5-diethylaminoethylamino-8 - methylthiochromanone; (4) 5 - amino - 8-methylthiochromanone is acetylated, treated with sulphuryl chloride in methylene chloride and then with dimethylaniline giving 5-amino-8-methylthiochromone which is converted to 5-diethylaminoethylamino - 8 - methylthiochromone hydrochloride; similarly (5), are prepared the 2,8 - dimethyl - and 2 - ethyl - 8 - methyl-derivatives; (6) 5 - acetamino - 8 - methylthiochromanone is treated with p-nitrosodimethylaniline in aqueous ethanolic KOH and the resulting 3-hydroxy-5-amino-8-methylthiochromone reacetylated, O-methylated with dimethyl sulphate and after hydrolysis the 3-methoxy - 5 - amino - 8 - methylthiochromone is converted to 3 - methoxy - 5 - diethylaminoethylamino - 8 - methylthiochromone; (7) b - (2 - methyl - 5 - aminophenylmercapto) propionic acid is esterified with ethanol-H2SO4, reacted with diethylaminoethyl chloride, refluxed with dilute HCl and then cyclized with H2SO4 to 5-diethylaminoethylamino-8-methylthiochromanone; (8) 2-methyl-5-chlorothiophenol is reacted with methyl methacrylate, the resulting methyl b -2-methyl-5-chlorophenylmercapto - isobutyrate saponified, cyclized to 5-chloro - 3,8 - dimethylthiochromanone and then reacted with diethylethylenediamine and copper powder yielding 5-diethylaminoethylamino-3,8-dimethylthiochromanone; (9) 5-chloro-8-methylthiochromanone prepared by method of (8) is converted by method of (6) to 3-methoxy-5-chloro - 8 - methylthiochromone and reacted with diethylethylenediamine giving 3-methoxy-5-diethylaminoethylamino - 8 - methylthiochromone; (10) to (19) the following 5-aminothiochromones are converted to the corresponding 5 - diethylaminoethylamino - thiochromones: 3,8 - dimethyl -, 2,3,8 - trimethyl -, 2,8 - dimethyl - 3 - ethyl -, 2,8 - dimethyl - 3 - propyl-, 2,8 - dimethyl - 3 - isopropyl -, 2 - phenyl - 8-methyl -, 3 - phenyl - 8 - methyl -, 2 - (21-chlorphenyl) - 8 - methyl -, 2 - (41 - chlorphenyl)-8 - methyl -, and 2 - (41 - methoxyphenyl) - 8-methyl.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE789430X | 1955-05-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB789430A true GB789430A (en) | 1958-01-22 |
Family
ID=6699678
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB13238/56A Expired GB789430A (en) | 1955-05-04 | 1956-04-30 | Derivatives of amino-thiochromanones and amino-thiochromones |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB789430A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3115793A (en) * | 1961-02-09 | 1963-12-31 | Hobbs Transmission Ltd | Power transmission apparatus |
-
1956
- 1956-04-30 GB GB13238/56A patent/GB789430A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3115793A (en) * | 1961-02-09 | 1963-12-31 | Hobbs Transmission Ltd | Power transmission apparatus |
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