GB551207A - Improvements in and relating to the manufacture of sulphonamido compounds - Google Patents
Improvements in and relating to the manufacture of sulphonamido compoundsInfo
- Publication number
- GB551207A GB551207A GB7286/42A GB728642A GB551207A GB 551207 A GB551207 A GB 551207A GB 7286/42 A GB7286/42 A GB 7286/42A GB 728642 A GB728642 A GB 728642A GB 551207 A GB551207 A GB 551207A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethylpyrimidine
- amino
- prepared
- chloride
- oxidizing
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Abstract
551,207. Aryl sulphenamides and sulphonamides. MANCHESTER OXIDE CO., Ltd., BANN, B., KRUG, P., WHEELER, D. E., TAYLOR, W., and GLADDING, G. April 29, 1941, Nos. 7286/42, 7287/42, [both divided out of 553,269], and 7079/42. [Class 2 (iii)] Benzenesulphonamidopyrimidines and p-substituted derivatives thereof are prepared by the oxidation of the corresponding sulphenamides, e.g. with alkali or alkaline earth permanganate or hypochlorite. The sulphenamides may be obtained by treating a diphenyldisulphide with chlorine in a non-aqueous medium and reacting the resulting sulphenyl chloride with an aminopyrimidine; the diphenyldisulphides may be prepared by heating with caustic alkali a thiocyanobenzene obtainable as described in Specifications 513,473 and 514,203. The sulphenamides may also be prepared by reacting a benzenesulphenyl ester or a benzenesulphenamide with an aminopyrimidine. The substituent in the p-position is preferably a halogen atom or a nitrogencontaining group convertible into an amino group, e.g. an acylamino or nitro group, and the products may be converted into the amino compounds which are useful therapeutically. According to the examples, (1) 2-benzenesulphonamido-4 : 6-dimethylpyrimidine is prepared by treating benzenesulphenyl chloride, obtained by chlorinating diphenyldisulphide in chloroform, with 2-amino-4 : 6-dimethvlpyrimidine and oxidizing the product with aqueous potassium permanganate ; (2) 2-(41- nitrobenzenesulphonamido)-4 : 6-dimethylpyrimidine is obtained by chlorinating 4 : 4<SP>1</SP>-dinitrodiphenyldisulphide in chloroform, converting the resulting p-nitrobenzenesulphenyl chloride into p-nitrobenzenesulphenic acid ethyl ester by treatment with sodium ethoxide, re-acting it with 2-amino-4 : 6-dimethylpyrimidine and oxidizing the sulphenamido product with potassium permanganate; (3) 2-(41-aminobenzenesulphonamido)-pyrimidine results when p-nitrobenzenesulphenyl chloride is .treated with 2-aminopyrimidine and the sulphenamido product oxidized with potassium permanganate to the corresponding sulphonamide which is then reduced with iron and hydrochloric acid ; by using 2-amino-4 : 6-dimethylpyrimidine in this process, 2-(4<SP>1</SP>-aminobenzenesulphonamido)- 4 : 6-dimethylpyrimidine is obtained; calcium permanganate or sodium hypochlorite solution may be employed in place of potassium permanganate ; (4) 2-(4<SP>1</SP>-nitrobenzenesulphonamido)-4: 6-dimethylpyrimidine is also obtained by heating p-nitrobenzenesulphenamide with 2-amino-4 : 6-dimethylpyrimidine in benzene and oxidizing the sulphenamido-pyrimidine so formed ; (5) 2-(4<SP>1</SP>-aminobenzenesulphonamido)- 4 : 6-dimethylpyrimidine is prepared by treating p-acetylaminobenzenesulphenyl chloride, obtained by chlorinating 4 : 4<SP>1</SP>-diacetylaminodiphenyldisulphide in chloroform, with 2-amino- 4 : 6-dimethylpyrimidine, oxidizing the resulting sulphenamide with potassium permanganate and hydrolysing the product; (6) 2-(41-chlorobenzenesulphonamido)-4 : 6-dimethylpyrimidine is prepared by chlorinating 4 : 4<SP>1</SP>-dichlorodiphenyldisulphide in chloroform, reacting the resulting p-chlorobenzenesulphenyl chloride with 2-amino-4: 6-dimethylpyrimidine, and oxidizing the sulphenamide formed with potassium - permanganate ; the p-chloro group may be converted into amino by treatment with ammonia. Specification 379,683 also is referred to. The first Provisional Specification refers. to the production of the naphthyl compounds.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB7286/42A GB551207A (en) | 1941-04-29 | 1941-04-29 | Improvements in and relating to the manufacture of sulphonamido compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB7286/42A GB551207A (en) | 1941-04-29 | 1941-04-29 | Improvements in and relating to the manufacture of sulphonamido compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB551207A true GB551207A (en) | 1943-02-11 |
Family
ID=9830177
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7286/42A Expired GB551207A (en) | 1941-04-29 | 1941-04-29 | Improvements in and relating to the manufacture of sulphonamido compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB551207A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2417004A (en) * | 1943-04-09 | 1947-03-04 | Firm Of J R Geigy A G | Process for the manufacture of 4-aminobenzene-nu1-(3':4'-dimethylbenzoyl)-sulfonamide |
US2671804A (en) * | 1948-12-28 | 1954-03-09 | Phillips Petroleum Co | Preparation and use of alkylene polyamine sulfenamides and thiosulefnamides |
EP0065226A2 (en) * | 1981-05-07 | 1982-11-24 | Bayer Ag | Sulfenamides, process for their preparation, their utilisation as medicines and their preparation |
-
1941
- 1941-04-29 GB GB7286/42A patent/GB551207A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2417004A (en) * | 1943-04-09 | 1947-03-04 | Firm Of J R Geigy A G | Process for the manufacture of 4-aminobenzene-nu1-(3':4'-dimethylbenzoyl)-sulfonamide |
US2671804A (en) * | 1948-12-28 | 1954-03-09 | Phillips Petroleum Co | Preparation and use of alkylene polyamine sulfenamides and thiosulefnamides |
EP0065226A2 (en) * | 1981-05-07 | 1982-11-24 | Bayer Ag | Sulfenamides, process for their preparation, their utilisation as medicines and their preparation |
EP0065226A3 (en) * | 1981-05-07 | 1985-12-11 | Bayer Ag | Sulfenamides, process for their preparation, their utilisation as medicines and their preparation |
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