GB772582A - Production of branched chain sulphenamides - Google Patents

Production of branched chain sulphenamides

Info

Publication number
GB772582A
GB772582A GB18630/55A GB1863055A GB772582A GB 772582 A GB772582 A GB 772582A GB 18630/55 A GB18630/55 A GB 18630/55A GB 1863055 A GB1863055 A GB 1863055A GB 772582 A GB772582 A GB 772582A
Authority
GB
United Kingdom
Prior art keywords
amine
mercaptothiazole
molecular
salt
oxidizing agent
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
GB18630/55A
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 Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical 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 Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB772582A publication Critical patent/GB772582A/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

Abstract

N-alkyl sulphenamides are prepared by reacting in an aqueous medium and in presence of an oxidizing agent at least 1.4 molecular proportions of a branched-chain aliphatic primary amine with one molecular proportion of a water-soluble salt of a 2-mercaptothiazole, at least 1.2 molecular equivalents of mineral acid being added to the reaction mixture prior to commencing the addition of oxidizing agent, and the molecular proportion of amine employed being always in excess of the molecular proportion of mineral acid. The 2-mercaptothiazole salt is preferably an alkali metal salt (e.g. the sodium salt) and is preferably present as at least 13 per cent by weight of the reaction mixture. The oxidizing agent is preferably a water-soluble hypochlorite (e.g. sodium hypochlorite) and the reaction therewith is preferably conducted at a temperature of 45-50 DEG C. Sulphuric acid is exemplified as the mineral acid. Specified thiazoles are 2-mercaptothiazole, 2 - mercapto - 4 - methylthiazole and 2-mercaptobenzothiazole. Specified amines are isopropylamine, isobutylamine, tertiary-butyl-amine, branched-chain amylamines, 2-ethyl-hexylamine and 1 : 1 : 3 : 3-tetramethylbutyl-amine. The examples describe the preparation of N - tertiary - butyl - 2 - benzothiazole-sulphenamide, N - isopropyl - 2 - benzothiazole-sulphenamide and N - (1 : 1 : 3 : 3 - tetramethylbutyl) - 2 - benzothiazolesulphenamide.
GB18630/55A 1954-06-28 1955-06-28 Production of branched chain sulphenamides Expired GB772582A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US772582XA 1954-06-28 1954-06-28

Publications (1)

Publication Number Publication Date
GB772582A true GB772582A (en) 1957-04-17

Family

ID=22137022

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18630/55A Expired GB772582A (en) 1954-06-28 1955-06-28 Production of branched chain sulphenamides

Country Status (1)

Country Link
GB (1) GB772582A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1090665B (en) * 1957-05-08 1960-10-13 Ici Ltd Process for the preparation of N-alkyl-bis (benzthiazolyl-2-sulfen) -imides
US4258197A (en) * 1979-06-08 1981-03-24 Pennwalt Corporation Manufacture of sulfenamides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1090665B (en) * 1957-05-08 1960-10-13 Ici Ltd Process for the preparation of N-alkyl-bis (benzthiazolyl-2-sulfen) -imides
US4258197A (en) * 1979-06-08 1981-03-24 Pennwalt Corporation Manufacture of sulfenamides

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