US3892760A - Bis-(2-pyridyl-1-oxide) disulfide - Google Patents
Bis-(2-pyridyl-1-oxide) disulfide Download PDFInfo
- Publication number
- US3892760A US3892760A US466328A US46632874A US3892760A US 3892760 A US3892760 A US 3892760A US 466328 A US466328 A US 466328A US 46632874 A US46632874 A US 46632874A US 3892760 A US3892760 A US 3892760A
- Authority
- US
- United States
- Prior art keywords
- oxide
- alkali metal
- disulfide
- hydrogen peroxide
- bis
- 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 - Lifetime
Links
Classifications
-
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
Definitions
- 3,759,932 also generally discloses the preparation of a disulfide compound using an in.-situ preparation technique wherein? mercaptopyridine is not "isolated. -rWh-ile these references broadly disclose the preparati'on' of the disulfide, problems have arisen when using the alkali metal salt of Z-mercaptopyridine-l-oxide in an in-situ technique wherein the alkali metal salt was obtained by oxidizing 2-chloropyridine with permaleic acid ,to form the N- oxide followed by mercaptization to form the salt.
- oxidationby the; known techniques as shown for,example in U.S. Pat. No. 2,742,476 resulted in the formation of undesired by-products such as the alkali metal maleate and alkali-metal fumarate. This contaminated the desired disulfideproduct and lowered the yield.
- drosulfide in accordance with known procedures as disclosed if] Us; Pat. No. 2,686,786.1"he'key step in this invention is the oxidation ofjthe preparedlalkali metal salt of2-mercaptopyridinel' oxide using hydrogen peroxide and a reaction pH of about i to about 5.
- a reaction pH of about i to about 5.
- the hydrogen peroxide concentration may be varied with about 5 to about 30 percent in aqueous solution being generally used. Generally a stoichiometi' ric. ratio of the alkali metal salt of 2-mercaptopyridine and hydrogen peroxide of about 2 moles of the mercaptopyri dine salt to about 1 mole of peroxide or a slight excess of up to about 15 percent peroxide is used.
- the pH of the reaction mixture is generally adjusted before the peroxide oxidation step by using any suitable acidifying agent such as the non-oxidizing mineral acids such as HCl andthe non-oxidizing organic acids.
- the 'disulf ed compounds prepared in accordance with the method of this invention have a variety of known uses, particularly as antibacterialand antifungal agentsin a variety of applications such as to combat agricultural plant diseases, and in plastics and fabrics to resist mildew or other fungus attack as disclosedin U.S. Pat. No. 2,742,476.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US466328A US3892760A (en) | 1974-05-02 | 1974-05-02 | Bis-(2-pyridyl-1-oxide) disulfide |
ZA00752024A ZA752024B (en) | 1974-05-02 | 1975-04-01 | Method for preparing bigs-(2-pyridyl-1-oxide) disufide |
IL46996A IL46996A (en) | 1974-05-02 | 1975-04-01 | Method for preparing bis-(2-pyridyl-1-oxide)disulfide |
IE716/75A IE41103B1 (en) | 1974-05-02 | 1975-04-02 | Method for preparing bis-(2-pyridyl-1-oxide) disulfide |
CA223,892A CA1052792A (en) | 1974-05-02 | 1975-04-04 | Method for preparing bis-(2-pyridyl-1-oxide) disulfide |
GB1439675A GB1469907A (en) | 1974-05-02 | 1975-04-08 | Method for preparing bis-2-pyridyl-1-oxide- disulphide |
AU79968/75A AU484367B2 (en) | 1974-05-02 | 1975-04-09 | METHOD FOR PREPARING BIS-(2-PYRIDYL-l-OXIDE DISULFIDE |
DK168275A DK143650C (da) | 1974-05-02 | 1975-04-18 | Fremgangsmaade til fremstilling af bis-(2-pyridyl-1-oxid)-disulfid |
NL7504696A NL7504696A (nl) | 1974-05-02 | 1975-04-21 | Werkwijze voor de bereiding van bis(2-pyridyl- -1-oxyde)disulfide. |
IT49240/75A IT1035419B (it) | 1974-05-02 | 1975-04-22 | Procedimento per la produzione di bis 2 piridil i ossido di sol furo |
FI751253A FI58917C (fi) | 1974-05-02 | 1975-04-25 | Foerfarande foer framstaellning av bis-(2-pyridyl-1-oxid)disulfid |
BR3288/75D BR7502591A (pt) | 1974-05-02 | 1975-04-29 | Aperfeicoamento em processo de preparar dissulfeto de bis-(1-oxido de 2-piridila) |
CH554575A CH597190A5 (ja) | 1974-05-02 | 1975-04-30 | |
FR7513649A FR2269525B1 (ja) | 1974-05-02 | 1975-04-30 | |
JP5307175A JPS5421344B2 (ja) | 1974-05-02 | 1975-05-01 | |
SE7505136A SE401508B (sv) | 1974-05-02 | 1975-05-02 | Forfarande for framstellning av bis(2-pyridyl-1-oxid)-disulfid |
DE19752519715 DE2519715C3 (de) | 1974-05-02 | 1975-05-02 | Verfahren zur Herstellung von Bis-(2-pyridyl-l-oxid)-disulfid |
BE156038A BE828695A (fr) | 1974-05-02 | 1975-05-02 | Preparation du bis-(2-pyridyl-1-oxyde) disulfure |
AR20854677D AR208546A1 (es) | 1974-05-02 | 1977-02-15 | Metodo de preparacion de disulfuro de bis-(2-piridil-1-oxido) |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US466328A US3892760A (en) | 1974-05-02 | 1974-05-02 | Bis-(2-pyridyl-1-oxide) disulfide |
Publications (1)
Publication Number | Publication Date |
---|---|
US3892760A true US3892760A (en) | 1975-07-01 |
Family
ID=23851343
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US466328A Expired - Lifetime US3892760A (en) | 1974-05-02 | 1974-05-02 | Bis-(2-pyridyl-1-oxide) disulfide |
Country Status (17)
Country | Link |
---|---|
US (1) | US3892760A (ja) |
JP (1) | JPS5421344B2 (ja) |
AR (1) | AR208546A1 (ja) |
BE (1) | BE828695A (ja) |
BR (1) | BR7502591A (ja) |
CA (1) | CA1052792A (ja) |
CH (1) | CH597190A5 (ja) |
DK (1) | DK143650C (ja) |
FI (1) | FI58917C (ja) |
FR (1) | FR2269525B1 (ja) |
GB (1) | GB1469907A (ja) |
IE (1) | IE41103B1 (ja) |
IL (1) | IL46996A (ja) |
IT (1) | IT1035419B (ja) |
NL (1) | NL7504696A (ja) |
SE (1) | SE401508B (ja) |
ZA (1) | ZA752024B (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4504667A (en) * | 1983-06-24 | 1985-03-12 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
US4585871A (en) * | 1982-03-26 | 1986-04-29 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
US6664280B2 (en) | 2001-07-25 | 2003-12-16 | The United States Of America As Represented By The Secretary Of The Army | Antivesicant compounds and methods of making and using thereof |
US20040171600A1 (en) * | 2001-03-06 | 2004-09-02 | Toshimasa Ohnishi | Antimicrobial compositions |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2686786A (en) * | 1953-01-09 | 1954-08-17 | Olin Mathieson | Nu-hydroxy-2-pyridinethiones and method of preparing same |
US2742476A (en) * | 1953-10-26 | 1956-04-17 | Olin Mathieson | Derivatives of 2-mercaptopyridine 1-oxide |
US2951844A (en) * | 1958-11-05 | 1960-09-06 | Olin Mathieson | Cyclic process for manufacture of 2-chloropyridine-1-oxide |
US3759932A (en) * | 1972-08-25 | 1973-09-18 | Olin Corp | Method for preparing mercaptopyridines using alkali metal polysulfides |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1224744B (de) * | 1956-04-13 | 1966-09-15 | Olin Mathieson | Verfahren zur Herstellung von baktericiden und fungiciden schwefelhaltigen Pyridinverbindungen |
-
1974
- 1974-05-02 US US466328A patent/US3892760A/en not_active Expired - Lifetime
-
1975
- 1975-04-01 ZA ZA00752024A patent/ZA752024B/xx unknown
- 1975-04-01 IL IL46996A patent/IL46996A/en unknown
- 1975-04-02 IE IE716/75A patent/IE41103B1/xx unknown
- 1975-04-04 CA CA223,892A patent/CA1052792A/en not_active Expired
- 1975-04-08 GB GB1439675A patent/GB1469907A/en not_active Expired
- 1975-04-18 DK DK168275A patent/DK143650C/da not_active IP Right Cessation
- 1975-04-21 NL NL7504696A patent/NL7504696A/xx not_active Application Discontinuation
- 1975-04-22 IT IT49240/75A patent/IT1035419B/it active
- 1975-04-25 FI FI751253A patent/FI58917C/fi not_active IP Right Cessation
- 1975-04-29 BR BR3288/75D patent/BR7502591A/pt unknown
- 1975-04-30 FR FR7513649A patent/FR2269525B1/fr not_active Expired
- 1975-04-30 CH CH554575A patent/CH597190A5/xx not_active IP Right Cessation
- 1975-05-01 JP JP5307175A patent/JPS5421344B2/ja not_active Expired
- 1975-05-02 BE BE156038A patent/BE828695A/xx unknown
- 1975-05-02 SE SE7505136A patent/SE401508B/xx unknown
-
1977
- 1977-02-15 AR AR20854677D patent/AR208546A1/es active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2686786A (en) * | 1953-01-09 | 1954-08-17 | Olin Mathieson | Nu-hydroxy-2-pyridinethiones and method of preparing same |
US2742476A (en) * | 1953-10-26 | 1956-04-17 | Olin Mathieson | Derivatives of 2-mercaptopyridine 1-oxide |
US2951844A (en) * | 1958-11-05 | 1960-09-06 | Olin Mathieson | Cyclic process for manufacture of 2-chloropyridine-1-oxide |
US3759932A (en) * | 1972-08-25 | 1973-09-18 | Olin Corp | Method for preparing mercaptopyridines using alkali metal polysulfides |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4585871A (en) * | 1982-03-26 | 1986-04-29 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
US4504667A (en) * | 1983-06-24 | 1985-03-12 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
US20040171600A1 (en) * | 2001-03-06 | 2004-09-02 | Toshimasa Ohnishi | Antimicrobial compositions |
US7416736B2 (en) * | 2001-03-06 | 2008-08-26 | Janssen Pharmaceutica N.V. | Antimicrobial compositions |
US6664280B2 (en) | 2001-07-25 | 2003-12-16 | The United States Of America As Represented By The Secretary Of The Army | Antivesicant compounds and methods of making and using thereof |
Also Published As
Publication number | Publication date |
---|---|
AU7996875A (en) | 1976-10-14 |
DE2519715B2 (de) | 1977-03-31 |
AR208546A1 (es) | 1977-02-15 |
NL7504696A (nl) | 1975-11-04 |
SE7505136L (sv) | 1975-11-03 |
IE41103B1 (en) | 1979-10-24 |
SE401508B (sv) | 1978-05-16 |
JPS50149680A (ja) | 1975-11-29 |
DE2519715A1 (de) | 1975-11-06 |
FI751253A (ja) | 1975-11-03 |
DK143650B (da) | 1981-09-21 |
ZA752024B (en) | 1976-02-25 |
IT1035419B (it) | 1979-10-20 |
CA1052792A (en) | 1979-04-17 |
BE828695A (fr) | 1975-11-03 |
CH597190A5 (ja) | 1978-03-31 |
JPS5421344B2 (ja) | 1979-07-30 |
BR7502591A (pt) | 1976-03-16 |
IL46996A (en) | 1977-12-30 |
DK168275A (da) | 1975-11-03 |
GB1469907A (en) | 1977-04-06 |
DK143650C (da) | 1982-02-15 |
FI58917B (fi) | 1981-01-30 |
FI58917C (fi) | 1981-05-11 |
FR2269525B1 (ja) | 1979-10-05 |
FR2269525A1 (ja) | 1975-11-28 |
IE41103L (en) | 1975-11-02 |
IL46996A0 (en) | 1975-06-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4396766A (en) | Process for producing sodium and zinc pyrithione | |
US3892760A (en) | Bis-(2-pyridyl-1-oxide) disulfide | |
JPS6114148B2 (ja) | ||
US4382040A (en) | Process for production of 2,3-dimercaptopropane-1-sulfonic acid and its salts | |
US4113767A (en) | Process for the preparation of alkali metal salts of 3,3-dimethyl-2-oxo-butyric acid | |
US2644005A (en) | Organic arsenical compounds | |
US2657231A (en) | Process for producing alkylene-bis-dithio-alkylene and -arylene-dicarboxylic acids | |
US2544904A (en) | Pyridine compounds and method for their production | |
US3641033A (en) | 4 4' - (lower-alkylenedithio or disulfonyl)-bis-tetrahalo pyridines and derivatives thereof | |
US3632825A (en) | Nickel alkoxide compounds and process for preparation thereof | |
US4151355A (en) | Process for the preparation of 6-tert.-butyl-3-mercapto-4-amino-1,2,4-triazin-5(4H)-one | |
EP0353944B1 (en) | Aminocarbonyl-substituted pyridinesulfinic acid or salts thereof | |
US2409291A (en) | Chemotherapeutic sulfanilamide derivatives | |
US4022830A (en) | Process for preparing polychlorobenzamide derivatives | |
US4336390A (en) | Benzoxazolone preparation | |
US4256892A (en) | Preparation of bis-2-pyridyl-disulfides | |
US3501486A (en) | Process for the production of 2-pyridine aldoximes | |
US3654292A (en) | Manufacture of 3 5-dichloro-2 6-difluoro - 4 - hydroxypyridine and salts thereof | |
EP0195738B1 (en) | Process for the preparation of n,n -diisopropyl-2-benzothiazyl-sulfenamide | |
US4173581A (en) | Process for the preparation of alkylthiosemicarbazides | |
JP2717842B2 (ja) | アミノカルボニル置換ピリジンスルフィン酸又はその塩 | |
JPH0725539B2 (ja) | ジシアナミド金属塩の製造方法 | |
US2914555A (en) | 4-alkylphenyl esters of 4-chlorobenzoic acid | |
US3310568A (en) | Process for preparing esters of pyridine thiones | |
KR100456092B1 (ko) | 글라이옥살과 암모늄염을 사용하는2,2'-바이-1h-이미다졸의 제조방법 |