GB1389768A - Production of aminodithioazoles - Google Patents

Production of aminodithioazoles

Info

Publication number
GB1389768A
GB1389768A GB1225373A GB1225373A GB1389768A GB 1389768 A GB1389768 A GB 1389768A GB 1225373 A GB1225373 A GB 1225373A GB 1225373 A GB1225373 A GB 1225373A GB 1389768 A GB1389768 A GB 1389768A
Authority
GB
United Kingdom
Prior art keywords
morpholinodithio
benzothiazole
methylthiazole
dissociation constant
march
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
GB1225373A
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.)
Monsanto Co
Original Assignee
Monsanto Co
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 Monsanto Co filed Critical Monsanto Co
Publication of GB1389768A publication Critical patent/GB1389768A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/76—Sulfur atoms attached to a second hetero atom
    • C07D277/78—Sulfur atoms attached to a second hetero atom to a second sulphur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/76—Sulfur atoms attached to a second hetero atom
    • C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom

Abstract

1389768 Azole derivatives MONSANTO CO 14 March 1973 [15 March 1972] 12253/73 Heading C2C Aminodithioazoles are prepared by reacting azolesulphenamides with sulphur in the presence as catalyst of a base comprising an alkali metal derivative of a proton-donor compound having a dissociation constant or first dissociation constant equal to or less than the first dissociation constant of H 3 PO 4 (1À6 Î 10<SP>-2</SP>). Specified bases include hydroxides, alcoholates, thiocyanates, phosphates, carbonates, alkanoates, azolemercaptides, dithiocarbamates, xanthates, thiophenolates, alkylmercaptides and dithioalkanoates. In a modification the amido group of the sulphenamide may be replaced in the product by another amine present during the reaction. Examples prepare 2-(morpholinodithio)benzothiazole, 2 - (morpholinodithio)benzimidazole, 2 - (morpholinodithio)benzoxazole, 2 - (morpholinodithio) - 5 - chlorobenzothiazole, 2- (morpholinodithio) - 6 - ethoxybenzothiazole, 2 - (morpholinodithio) - 6 - nitrobenzothiazole, 2 - (morpholinodithio) - 4 - methylthiazole, 2 - (morpholinodithio) - 5 - acetyl - 4 - methylthiazole, 2 - (morpholinodithio) - 5 - ethoxycarbonyl - 4 - methylthiazole, 2 - (2,6 - dimethylmorpholinodithio)benzothiazole, 2,2<SP>1</SP>- (1,4 - piperazinediylbisdithio)bis - benzothiazole, 2 - (1,2,3,4 - tetrahydro - 2 - isoquinolinyldithio)benzothiazole, 2 - (1,2,3,4,4a,5,6,7,- 8,8a - decahydro - 1 - quinolinyldithio)benzothiazole, a 2 - (1 - indolinyldithio)benzothiazole, 2 - [4 - (3 - phenylpropyl)piperidinothio]- benzothiazole. Ethyl 4 - (2 - benzothiazolyldithio)piperazine carboxylate, 2 - (4 - benzyl - 1- piperazinyldithiobenzothiazole and 2 - (1- pyrrolidinyldithio)benzothiazole. 2 - Morpholinothiobenzothiazole is prepared by heating morpholine with N-t-butyl-2-benzothiazolesulphenamide.
GB1225373A 1972-03-15 1973-03-14 Production of aminodithioazoles Expired GB1389768A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US23508172A 1972-03-15 1972-03-15

Publications (1)

Publication Number Publication Date
GB1389768A true GB1389768A (en) 1975-04-09

Family

ID=22884027

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1225373A Expired GB1389768A (en) 1972-03-15 1973-03-14 Production of aminodithioazoles

Country Status (2)

Country Link
BE (1) BE796764A (en)
GB (1) GB1389768A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2161160B (en) * 1984-07-06 1989-05-24 Fisons Plc Heterocyclic sulphinyl compounds
DE4032680A1 (en) * 1990-10-15 1992-04-16 Akzo Gmbh METHOD FOR PRODUCING 2-AMINODITHIOTHIAZOLES AND 2-AMINOTRITHIOTHIAZOLES

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112851914B (en) * 2021-01-11 2022-08-26 安徽工业大学 Composite modified 2-methylimidazole curing agent and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2161160B (en) * 1984-07-06 1989-05-24 Fisons Plc Heterocyclic sulphinyl compounds
DE4032680A1 (en) * 1990-10-15 1992-04-16 Akzo Gmbh METHOD FOR PRODUCING 2-AMINODITHIOTHIAZOLES AND 2-AMINOTRITHIOTHIAZOLES

Also Published As

Publication number Publication date
BE796764A (en) 1973-09-14

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee