GB737252A - Improvements relating to 2-benzothiazolyl sulfene morpholide - Google Patents

Improvements relating to 2-benzothiazolyl sulfene morpholide

Info

Publication number
GB737252A
GB737252A GB32976/53A GB3297653A GB737252A GB 737252 A GB737252 A GB 737252A GB 32976/53 A GB32976/53 A GB 32976/53A GB 3297653 A GB3297653 A GB 3297653A GB 737252 A GB737252 A GB 737252A
Authority
GB
United Kingdom
Prior art keywords
morpholine
chloromorpholine
toluene
acid acceptor
solvent
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
GB32976/53A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid 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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB737252A publication Critical patent/GB737252A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

2-Benzothiazyl sulphene morpholide is manufactured by treating 2-benzothiazolyl disulphide in an inert organic solvent with at least an equimolecular proportion each of N-chloromorpholine and of morpholine in the presence of an acid acceptor. Preferred solvents are hydrocarbons and halogenated hydrocarbons of the benzene series, whilst the acid acceptor is advantageously an amine, preferably a tertiary amine or excess of morpholine. The N-chloromorpholine may be prepared by chlorinating morpholine in situ in the solvent to be used in the condensation. The acid acceptor may be regenerated for further use by treating it, either in the reaction mixture or after separation and re-slurrying in an anhydrous inert solvent, with ammonia and separating the ammonium chloride formed. When morpholine is used it may be chlorinated before being recycled. In examples (1) 1 mol. of 2-benzothiazolyl disulphide is added to a solution of 1 mol. of N-chloromorpholine and 2 mols. of morpholine in toluene, which is then stirred at 30-45 DEG C., after which the mixture is saturated with anhydrous ammonia, the ammonium chloride formed is filtered off, morpholine is extracted with water and the toluene steam distilled; (2) the toluene in (1) is replaced by chlorobenzene and the proportion of morpholine is increased slightly.
GB32976/53A 1952-12-12 1953-11-27 Improvements relating to 2-benzothiazolyl sulfene morpholide Expired GB737252A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US325699A US2730527A (en) 1952-12-12 1952-12-12 Preparation of 2-benzothiazolyl sulfene morpholide

Publications (1)

Publication Number Publication Date
GB737252A true GB737252A (en) 1955-09-21

Family

ID=23269035

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32976/53A Expired GB737252A (en) 1952-12-12 1953-11-27 Improvements relating to 2-benzothiazolyl sulfene morpholide

Country Status (5)

Country Link
US (1) US2730527A (en)
DE (1) DE1013653B (en)
ES (1) ES212646A2 (en)
FR (1) FR64850E (en)
GB (1) GB737252A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1175239B (en) * 1955-11-30 1964-08-06 American Cyanamid Co Process for the production of sulfenic morpholides
EP0202511A1 (en) * 1985-05-11 1986-11-26 Bayer Ag Process for the preparation of benzothiazole sulfene amides

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3126394A (en) * 1964-03-24 Crystallizing z
US3070599A (en) * 1962-12-25 Method fos preparing secondary amino-
US3022300A (en) * 1954-09-23 1962-02-20 Goodyear Tire & Rubber Method of preparing sulfenamides
US2816881A (en) * 1955-07-08 1957-12-17 American Cyanamid Co Method of vulcanizing a rubber in the presence of an accelerator and the product obtained thereby
US2839531A (en) * 1955-09-19 1958-06-17 Ici Ltd Process for preparing 2-benzthiazylsulfeno morpholide
US2871239A (en) * 1955-12-27 1959-01-27 Monsanto Chemicals 2-(2,6-dimethyl-4-morpholinylmercapto)-benzothiazoles
US3086018A (en) * 1957-12-24 1963-04-16 Goodyear Tire & Rubber Manufacture of amino thiazole disulfides
US3055909A (en) * 1960-01-13 1962-09-25 American Cyanamid Co Preparation of n-cyclohexyl-2-benzothiazole sulfenamide
CA3023244C (en) 2016-05-10 2023-12-19 Huntsman Advanced Materials Americas Llc Benzothiazoles as latent catalysts for benzoxazine resins

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2045888A (en) * 1936-06-30 Preparation of sulphene amides
US2271834A (en) * 1939-03-03 1942-02-03 Firestone Tire & Rubber Co Method of treating mercaptothiazoles with ammonia derivatives
US2261024A (en) * 1939-06-22 1941-10-28 Us Rubber Co Vulcanization accelerator

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1175239B (en) * 1955-11-30 1964-08-06 American Cyanamid Co Process for the production of sulfenic morpholides
EP0202511A1 (en) * 1985-05-11 1986-11-26 Bayer Ag Process for the preparation of benzothiazole sulfene amides

Also Published As

Publication number Publication date
FR64850E (en) 1955-12-02
ES212646A2 (en) 1955-03-01
DE1013653B (en) 1957-08-14
US2730527A (en) 1956-01-10

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