GB609919A - A process for the manufacture of 4.2-(substituted thiazolinyl)-2-substituted-oxazolones - Google Patents
A process for the manufacture of 4.2-(substituted thiazolinyl)-2-substituted-oxazolonesInfo
- Publication number
- GB609919A GB609919A GB915946A GB915946A GB609919A GB 609919 A GB609919 A GB 609919A GB 915946 A GB915946 A GB 915946A GB 915946 A GB915946 A GB 915946A GB 609919 A GB609919 A GB 609919A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbomethoxy
- dimethyl
- methyl
- solution
- alcohol
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
4-21-(Substituted thiazolinyl)-2-substituted-oxazolones of the general formula <FORM:0609919/IV(b)/1> or a tautomeric form thereof (wherein R1 represents hydrogen or a methyl group, R2 a methyl group, and R4 an alkyl, aryl or aralkyl group which may contain substituents) are manufactured by heating a compound of the general formula <FORM:0609919/IV(b)/2> (wherein R3 represents an alkyl or aralkyl group) with phosphorous pentachloride, oxychloride or trichloride or mixtures thereof in the presence of a solvent. Examples describe the heating with phosphorus pentachloride and chloroform, under reflux, of 4-carbomethoxy-5 : 5-dimethyl-2-(phenylacetamido-, p - nitrobenzamido- and n-caproamido-carbobenzoxy and -carbethoxy)-methylthiazoline (i.e. compounds of the second general formula above, in which R1=R2=CH3, R3= - CH2.C6H5 or - C2H5 and R4 = - CH2.C6H5, - C6H4 - NO2(p or n-C5H11) to produce 4-21-(51 : 51-dimethyl-41-carbomethoxythiazolinyl)-2-benzyl-, 2-p-nitrophenyl- and 2-n-amyloxazolone. 2-(Acylamido-carboalkoxy or -carboaralkoxy)-methylthiazolines, of the second general formula above, are obtainable by the action of the appropriate acid chloride in ether in the presence of sodium bicarbonate on the corresponding free amino compounds (or their salts), which compounds may in turn be made by nitrosation and reduction from the corresponding 4-carbomethoxy-5-methyl- or 5 : 5-dimethyl - 2 - carboalkoxy - or - carboaralkoxymethylthiazolines. When R3 is alkyl, the nitrosation may be effected by adding sodium nitrite solution to a cooled alcoholic solution of the starting material in the presence of acid (e.g. acetic or preferably hydrochloric acid), and the reduction by catalytic methods or preferably by warming with an ammoniacal solution of sodium hydrosulphite. When R3 is aralkyl, the nitrosation may be effected by addition of sodium nitrite to a solution of the starting material in acetic acid, and the reduction by means of aluminium amalgam and alcohol. In examples: (1) 4-carbomethoxy-5 : 5-dimethyl-2-carbobenzoxymethylthiazoline is treated with sodium nitrite and acetic acid in dioxane, and the resulting nitroso compound is refluxed with aluminium amalgam and alcohol in ether to form 4-carbomethoxy-5 : 5 - dimethyl - 2 - (amino - carbobenzoxy)-methylthiazoline (isolated in the form of its oxalate); (2) 2 - carbethoxymethyl - 4 - carbomethoxy-5 : 5-dimethylthiazoline is treated with sodium nitrite solution and dilute hydrochloric acid in alcohol, and the resulting nitroso compound is warmed with aqueous ammonia and sodium hydrosulphite solution to give 2-(amino-carbethoxy)-methyl-4-carbomethoxy-5 : 5-dimethylthiazoline (isolated as the hydrochloride or oxalate); (3) to (8) the products of (1) and (2) (oxalate) are treated in ether in the presence of sodium bicarbonate with n-caproyl, phenylacetyl or p-nitrobenzoyl chloride. Specification 590,040 is referred to. 4 - Carbomethoxy - 5 - methyl - or 5 : 5 - dimethyl-2-carbobenzoxymethylthiazolines are obtainable by treating benzyl cyanoacetate with absolute alcohol and dry hydrogen chloride and condensing the resulting imino-ether hydrochloride with the appropriate b -mono- or di-substituted cysteine methyl ester, e.g. penicillamine methyl ester (R1=R2=CH3). Benzyl cyanoacetate is prepared by heating ethyl cyanoacetate with benzyl alcohol.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB915946A GB609919A (en) | 1946-03-25 | 1946-03-25 | A process for the manufacture of 4.2-(substituted thiazolinyl)-2-substituted-oxazolones |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB915946A GB609919A (en) | 1946-03-25 | 1946-03-25 | A process for the manufacture of 4.2-(substituted thiazolinyl)-2-substituted-oxazolones |
Publications (1)
Publication Number | Publication Date |
---|---|
GB609919A true GB609919A (en) | 1948-10-08 |
Family
ID=9866544
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB915946A Expired GB609919A (en) | 1946-03-25 | 1946-03-25 | A process for the manufacture of 4.2-(substituted thiazolinyl)-2-substituted-oxazolones |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB609919A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4371734A (en) | 1978-01-17 | 1983-02-01 | Basf Aktiengesellschaft | Preparation of thiazole derivatives |
-
1946
- 1946-03-25 GB GB915946A patent/GB609919A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4371734A (en) | 1978-01-17 | 1983-02-01 | Basf Aktiengesellschaft | Preparation of thiazole derivatives |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB670610A (en) | Manufacture of a new imidazoline | |
US2401522A (en) | Aromatic carboxylic acid amides and a process for their manufacture | |
GB609919A (en) | A process for the manufacture of 4.2-(substituted thiazolinyl)-2-substituted-oxazolones | |
NO127054B (en) | ||
GB1196456A (en) | Process for the Production of Heterocyclic Thiophosphoric and Thiophosphonic Acid Esters | |
GB1064132A (en) | New quinoline derivatives, process for their production and use thereof in the production of carbostyril derivatives | |
US2422888A (en) | Pyrimidine compounds and method of | |
GB828847A (en) | Improvements in or relating to cyanine dyes | |
GB1091448A (en) | Novel d-threo-1-phenyl-2-aminopropan-1,3-diol derivatives and a process for their production | |
GB664550A (en) | Stabilizers for photographic emulsions | |
RU2485083C1 (en) | Method of producing substituted pyrimidin-5-yl carboxylic acids | |
Baltzly et al. | Synthetic Analogs of Oxytocic Drugs. III. Homologs of the Phenethyl β-Alanine Type | |
GB1017979A (en) | Improvements in or relating to the preparation of chloro-acetoacetamides and to substituted dioxolan derivatives of acetic acid esters as intermediates in said preparation | |
GB744868A (en) | Improvements relating to 4-amino-5-formamido-6-disubstituted-aminopyrimidines and acid addition salts thereof | |
GB642277A (en) | A process for the preparation of 2,5-diacyloxy-2,5-dihydrofurans | |
GB735454A (en) | Improvements in or relating to threo-aminodiols and intermediates therefor | |
ES403922A1 (en) | A procedure for the production of derivatives of oximetilicos esters. (Machine-translation by Google Translate, not legally binding) | |
GB1103155A (en) | Improvements in and relating to quinazolines | |
GB752332A (en) | Improvements in or relating to n, mono substituted piperazines and process of preparing the same | |
GB1034788A (en) | Process for the production of salts of substituted ª-amino carboxylic acids | |
GB672407A (en) | Dialkylaminoalkyl-p-hydroxybenzoate salts of penicillin and their production | |
GB701120A (en) | 3-substituted-3, 4-dihydro-coumarins and process for the manufacture thereof | |
GB613489A (en) | Improvements in process and culture medium for the production of penicillin | |
GB636145A (en) | Stabilizers for photographic silver-halide emulsions | |
GB633736A (en) | Improvements in or relating to the production of oxazolone derivatives |