GB345735A - Process for the manufacture of amino-aryl-thiazole-compounds - Google Patents

Process for the manufacture of amino-aryl-thiazole-compounds

Info

Publication number
GB345735A
GB345735A GB226630A GB226630A GB345735A GB 345735 A GB345735 A GB 345735A GB 226630 A GB226630 A GB 226630A GB 226630 A GB226630 A GB 226630A GB 345735 A GB345735 A GB 345735A
Authority
GB
United Kingdom
Prior art keywords
treated
amino
sulphuryl chloride
chlorobenzene
methyl
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
GB226630A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB226630A priority Critical patent/GB345735A/en
Publication of GB345735A publication Critical patent/GB345735A/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
    • C07D277/84—Naphthothiazoles
    • 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
    • C07D277/82—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Aminoarylthiazole compounds are manufactured by the action of chlorine or an agent yielding chlorine on thiourea derivatives of the general formula: aryl-NX-CS-NH2, where aryl indicates an aromatic residue, which may contain further substituents, and X hydrogen or an alkyl- or aryl-group. The products, in the case in which X is hydrogen, when treated at a temperature above 100 DEG C. with concentrated caustic alkali solution yield aminoarylmercaptans. As agents yielding chlorine are specified sulphuryl chloride, sulphur chloride, sulphur dichloride and antimony pentachloride, and as diluents chlorobenzene, carbon tetrachloride and glacial acetic acid. In examples: (1) phenylthiourea is treated with sulphuryl chloride in chlorobenzene solution to produce 2-aminobenzothiazole, which may be converted to 1-aminophenyl - 2 - mercaptan; (2) o - tolylthiourea similarly yields 2-amino-4-methylbenzothiazole; (3) the same reaction is carried out using excess of sulphuryl chloride without any other diluent; (4) 4-ethoxyphenylthiourea is treated with disulphur dichloride in chlorobenzene solution, yielding 2-amino-6-ethoxybenzothiazole; (5) the same reaction is effected by means of antimony pentachloride; (6) 2-methyl-4-chlorophenylthiourea (obtained by heating 2-methyl-4-chloraniline hydrochloride with ammonium thiocyanate) is treated with chlorine or sulphuryl chloride in chlorobenzene solution, producing 2-amino-4-methyl-6-chlorobenzothiazole; 2-methoxyphenylthiourea is similarly converted to 2-amino-4-methoxybenzothiazole; (7) b -naphthylthiourea, treated with sulphuryl chloride in chlorobenzene solution, yields 6 : 7-benzo - 2 - aminobenzothiazole; (8) p - tolylthiourea is converted, by the action of sulphuryl chloride in chlorobenzene or carbon tetrachloride solution, into 2-amino-6-methylbenzothiazole; (9) asymmetrical phenylmethylthiourea is treated with sulphuryl chloride in chlorobenzene solution to produce 2-imino-3-methyl-2 : 3-dihydrobenzothiazole; (10) asymmetrical diphenylthiourea similarly yields 2-imino-3-phenyl-2 : 3-dihydrobenzothiazole. Specification 306,590, [Class 2 (iii), Dyes &c.], is referred to.
GB226630A 1930-01-22 1930-01-22 Process for the manufacture of amino-aryl-thiazole-compounds Expired GB345735A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB226630A GB345735A (en) 1930-01-22 1930-01-22 Process for the manufacture of amino-aryl-thiazole-compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB226630A GB345735A (en) 1930-01-22 1930-01-22 Process for the manufacture of amino-aryl-thiazole-compounds

Publications (1)

Publication Number Publication Date
GB345735A true GB345735A (en) 1931-04-02

Family

ID=9736529

Family Applications (1)

Application Number Title Priority Date Filing Date
GB226630A Expired GB345735A (en) 1930-01-22 1930-01-22 Process for the manufacture of amino-aryl-thiazole-compounds

Country Status (1)

Country Link
GB (1) GB345735A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2475949A (en) * 1945-03-31 1949-07-12 Eastman Kodak Co beta-naphthoselenazole compounds
EP0003141A2 (en) * 1978-01-18 1979-07-25 Hoechst Aktiengesellschaft Process for the preparation of 2-amino-arylenothiazole compounds and their ring N-substituted derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2475949A (en) * 1945-03-31 1949-07-12 Eastman Kodak Co beta-naphthoselenazole compounds
EP0003141A2 (en) * 1978-01-18 1979-07-25 Hoechst Aktiengesellschaft Process for the preparation of 2-amino-arylenothiazole compounds and their ring N-substituted derivatives
EP0003141A3 (en) * 1978-01-18 1979-08-08 Hoechst Aktiengesellschaft Process for the preparation of 2-amino-arylenothiazole compounds and their ring n-substituted derivatives

Similar Documents

Publication Publication Date Title
US4670556A (en) Process for the production of thiazolyl-2-sulphenamides
GB345735A (en) Process for the manufacture of amino-aryl-thiazole-compounds
US2468952A (en) Process for the preparation of di-thiazyl disulfide
US2007335A (en) Process of producing o-aminoaryl mercaptans and derivatives thereof
US2119131A (en) Method of preparing dithiazyl disulphides
US3658830A (en) 5-(substituted mercapto sulfiny sulfonyl or sulfamoyl)
US2070523A (en) Process of preparing thiazyl derivatives
US2261024A (en) Vulcanization accelerator
US3244723A (en) Certain 4-aminothiazole compounds and their preparation
US2117120A (en) Manufacture of mercaptothiazoles
US2189720A (en) Vulcanization of rubber
US2034459A (en) Process of preparing aryl-mercaptans and derivatives thereof
US2033949A (en) Organic fluorine compounds
US2140272A (en) Method of preparing urea deriva
US2028082A (en) Method of preparing thiazyl monosulphides
US2304426A (en) Thiazyl sulphides
US2109158A (en) Mercaptazole derivatives and their process of preparation
US2060428A (en) Nitro-phenyl-arylene-thiazyl-disulphides and process of manufacturing the same
US1996011A (en) Method of reacting mercaptothiazoles with primary amines and formaldehyde
US2772279A (en) Preparation of sulfenamides
US2265319A (en) Manufacture of dithio-bis-thiazoles
US3071585A (en) Process for preparing 2, 6-dimethylmorpholinylmercaptobenzothiazole
US2263014A (en) Preparation of thiazoles
US1954707A (en) Preparation of 1-thioglycol 2-amino 5-alkoxy benzene derivatives
US2136332A (en) Vulcanization of rubber