GB585666A - Improvements in and relating to the manufacture of thioketones - Google Patents
Improvements in and relating to the manufacture of thioketonesInfo
- Publication number
- GB585666A GB585666A GB1123943A GB1123943A GB585666A GB 585666 A GB585666 A GB 585666A GB 1123943 A GB1123943 A GB 1123943A GB 1123943 A GB1123943 A GB 1123943A GB 585666 A GB585666 A GB 585666A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- dithioacetate
- ethyl
- thioacetylmethylene
- toluenesulphonate
- 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A thioketone is prepared by condensing a quaternary salt of a heterocyclic nitrogen base of the general formula <FORM:0585666/IV/1> wherein R is alkyl or substituted alkyl, R2 is H or alkyl, X is an anion, and either (1) a is O and Z the non-metallic atoms to complete a 5- or 6-membered ring containing the group <FORM:0585666/IV/2> wherein A and B are monovalent substituents or H, or together form a fused-on ring, or (2) a is 1 and Z is <FORM:0585666/IV/3> with an ester of a dithiocarboxylic acid. The reaction may be effected in presence of a basic condensing agent, and the group attached to the heterocyclic nitrogen atom may be an alkyl or substituted alkyl group (e.g. b -ethoxyethyl, allyl, or benzyl). Examples illustrate the production of 1-ethyl-2-thioacetylmethylene-1 : 2-dihydroquinoline from quinaldine etho-p-toluenesulphonate and methyl dithioacetate, of 3 - ethyl - 2 - thioacetylmethylene - benzthiazoline from 2 - methylbenzthiazoline etho-p-toluenesulphonate and methyl dithioacetate, of 5 - chloro - 3 - methyl - 2 - thiopropionyl - methylenebenzthiazoline from 5-chloro-2-methylbenzthiazole metho - p - toluenesulphonate and methyl dithiopropionate, of 1-ethyl-2-thioacetylmethylene-b -naphthathiazoline from 2-methyl-b -naphthathiazole etho-p-toluenesulphonate and methyl dithioacetate, of 3-ethyl-4-phenyl-2-thioacetylmethylene - 4 - thiazoline from 2 - methyl - 4 - phenylthiazole ethiodide and methyl dithioacetate, of 3 - (n - propyl) - 2 - thioacetylmethylenebenzthiazoline from 2-methylbenzthiazole n-propiodide and methyl dithioacetate, of 1-ethyl-4-thioacetylmethylene - 1 : 4 - dihydroquinoline from lepidine ethiodide and methyl dithioacetate, of 3-ethyl-2-thioacetylmethylene-a -naphthathiazoline from 2 - methyl - a - naphthathiazole etho - p - toluenesulphonate and methyl dithioacetate, of 3-ethyl-2-(a -(thioacetyl)-ethylidene)-benzthiazoline from 2-ethylbenzthiazole ethiodide and methyl dithioacetate, of 2 - cyclohexylthioformylmethy - lene - 3 - ethylbenzthiazoline from 2 - methylbenzthiazole etho - p - toluenesulphonate and the methyl ester of dithiocyclohexanecarboxylic acid, and of 1-phenyl-2-thioacetylmethylenebenzthiazoline from 2-methylbenzthiazole pheniodide and methyl dithioacetate. n-Butyl dithioacetate is prepared by reacting sodium dithioacetate with n-butyl bromide. According to the Provisional Specification, the thioketone may be prepared from a quaternary salt of a heterocyclic nitrogen base containing a R2-CH2- group (wherein R2 is H or alkyl) in the a - or g -position to the quaternary nitrogen atom. Specifications 533,425, 546,705, 551,331 and 566,010 are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1123943A GB585666A (en) | 1943-07-12 | 1943-07-12 | Improvements in and relating to the manufacture of thioketones |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1123943A GB585666A (en) | 1943-07-12 | 1943-07-12 | Improvements in and relating to the manufacture of thioketones |
Publications (1)
Publication Number | Publication Date |
---|---|
GB585666A true GB585666A (en) | 1947-02-18 |
Family
ID=9982552
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1123943A Expired GB585666A (en) | 1943-07-12 | 1943-07-12 | Improvements in and relating to the manufacture of thioketones |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB585666A (en) |
-
1943
- 1943-07-12 GB GB1123943A patent/GB585666A/en not_active Expired
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