US3892760A - Bis-(2-pyridyl-1-oxide) disulfide - Google Patents

Bis-(2-pyridyl-1-oxide) disulfide Download PDF

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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
Application number
US466328A
Other languages
English (en)
Inventor
Jr Haywood Hooks
James J Pitts
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.)
Olin Corp
Original Assignee
Olin Corp
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 Olin Corp filed Critical Olin Corp
Priority to US466328A priority Critical patent/US3892760A/en
Priority to ZA00752024A priority patent/ZA752024B/xx
Priority to IL46996A priority patent/IL46996A/en
Priority to IE716/75A priority patent/IE41103B1/xx
Priority to CA223,892A priority patent/CA1052792A/en
Priority to GB1439675A priority patent/GB1469907A/en
Priority to AU79968/75A priority patent/AU484367B2/en
Priority to DK168275A priority patent/DK143650C/da
Priority to NL7504696A priority patent/NL7504696A/xx
Priority to IT49240/75A priority patent/IT1035419B/it
Priority to FI751253A priority patent/FI58917C/fi
Priority to BR3288/75D priority patent/BR7502591A/pt
Priority to CH554575A priority patent/CH597190A5/xx
Priority to FR7513649A priority patent/FR2269525B1/fr
Priority to JP5307175A priority patent/JPS5421344B2/ja
Priority to SE7505136A priority patent/SE401508B/xx
Priority to DE19752519715 priority patent/DE2519715C3/de
Priority to BE156038A priority patent/BE828695A/xx
Application granted granted Critical
Publication of US3892760A publication Critical patent/US3892760A/en
Priority to AR20854677D priority patent/AR208546A1/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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)
US466328A 1974-05-02 1974-05-02 Bis-(2-pyridyl-1-oxide) disulfide Expired - Lifetime US3892760A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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