GB771850A - Novel sulphones and a process for the manufacture thereof - Google Patents

Novel sulphones and a process for the manufacture thereof

Info

Publication number
GB771850A
GB771850A GB19489/55A GB1948955A GB771850A GB 771850 A GB771850 A GB 771850A GB 19489/55 A GB19489/55 A GB 19489/55A GB 1948955 A GB1948955 A GB 1948955A GB 771850 A GB771850 A GB 771850A
Authority
GB
United Kingdom
Prior art keywords
phenacyl
bromide
sulphone
methobromide
pyridyl
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
Application number
GB19489/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB771850A publication Critical patent/GB771850A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0771850/IV(b)/1> and acid addition and salts thereof, wherein R stands for a hydrogen atom or an alkyl radical of one to six carbon atoms, "Aryl" stands for phenyl or a nuclear substituted phenyl radical, in which the substituent is a halogen atom, a nitro, hydroxy, cyano or amino radical, or an alkoxy, acyloxy or acylamido radical, containing as its characterizing moiety an alkyl group of 1 to 6 carbon atoms. The compounds are made by reacting an alkali-metal salt of pyridine-(3)-sulphinic acid with a phenacyl halide or a halogeno, cyano, nitro, alkoxy, acyloxy or acylamido substituted phenacyl halide, in an organic solvent and, if desired, hydrolysing the acyloxy, acylamido or alkoxy substituent and/or converting the compounds so obtained into acid addition or quaternary salts. Suitable organic solvents are ethanol, dimethyl-formamide, acetone and nitro-methane. When quaternary salts are required the free base may be treated, for example, with an alkyl halide, aralkyl halide or phenacyl halide. Examples describe the preparation of (1) phenacylpyridyl-(3)-sulphone and the corresponding quaternary methyl bromide, ethyl bromide, propyl bromide, butyl bromide, amyl bromide, p-nitrobenzyl bromide and phenacyl chloride; (2) a -methyl-phenacyl pyridyl-(3)-sulphone and its methobromide; (3) p-bromo-phenacyl pyridyl-3-sulphone and its methobromide; (4) p-methoxy-phenacyl pyridyl-(3)-sulphone and its methobromide; (5) p-acetoxy-phenacyl pyridyl-(3)-sulphone, its methobromide and, by hydrolysis, the corresponding 1 - methyl - 3 - (p - hydroxy - phenacyl - sulphonyl)-pyridinium bromide; (6) p-cyanophenacyl pyridyl-(3)-sulphone and its methobromide; (7) p-nitro-phenacyl pyridyl-(3)-sulphone and its methobromide and (8) p-acetamido - phenacyl pyridyl - (3) - sulphone, its methobromide and, by hydrolysis, the corresponding 1 - methyl - 3 - (p - aminophenacyl - sulphonyl)-pyridinium bromide hydrobromide. Phenacyl halides. p-Acetoxy-phenacyl bromide and p-cyano-phenacyl bromide are made by the action of bromide on p-acetoxy-acetophenone and/or p-cyano-acetophenone respectively.
GB19489/55A 1954-07-07 1955-07-06 Novel sulphones and a process for the manufacture thereof Expired GB771850A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US771850XA 1954-07-07 1954-07-07

Publications (1)

Publication Number Publication Date
GB771850A true GB771850A (en) 1957-04-03

Family

ID=22136565

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19489/55A Expired GB771850A (en) 1954-07-07 1955-07-06 Novel sulphones and a process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB771850A (en)

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