GB771850A - Novel sulphones and a process for the manufacture thereof - Google Patents
Novel sulphones and a process for the manufacture thereofInfo
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 125000001174 sulfone group Chemical group 0.000 title 1
- -1 alkyl radical Chemical class 0.000 abstract 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical group BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- IQNXUPDETFUQMO-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-(1-methylpyridin-1-ium-3-yl)sulfonylethanone bromide Chemical compound [Br-].C[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)O IQNXUPDETFUQMO-UHFFFAOYSA-N 0.000 abstract 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical group CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical group CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 abstract 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical group CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 abstract 1
- LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 abstract 1
- SMIOEQSLJNNKQF-UHFFFAOYSA-N 4-acetoxy acetophenone Chemical compound CC(=O)OC1=CC=C(C(C)=O)C=C1 SMIOEQSLJNNKQF-UHFFFAOYSA-N 0.000 abstract 1
- NLPHXWGWBKZSJC-UHFFFAOYSA-N 4-acetylbenzonitrile Chemical compound CC(=O)C1=CC=C(C#N)C=C1 NLPHXWGWBKZSJC-UHFFFAOYSA-N 0.000 abstract 1
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical group [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 abstract 1
- NISLWEGBICJBQZ-UHFFFAOYSA-N Br.[Br-].C[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)N Chemical compound Br.[Br-].C[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)N NISLWEGBICJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- SPCDJZGDCHUTIM-UHFFFAOYSA-N [4-(2-bromoacetyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(C(=O)CBr)C=C1 SPCDJZGDCHUTIM-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical group CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229940102396 methyl bromide Drugs 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical group ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
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.
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) |
-
1955
- 1955-07-06 GB GB19489/55A patent/GB771850A/en not_active Expired
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