GB1020034A - Chloroalkyl thiazoles - Google Patents

Chloroalkyl thiazoles

Info

Publication number
GB1020034A
GB1020034A GB35141/62A GB3514162A GB1020034A GB 1020034 A GB1020034 A GB 1020034A GB 35141/62 A GB35141/62 A GB 35141/62A GB 3514162 A GB3514162 A GB 3514162A GB 1020034 A GB1020034 A GB 1020034A
Authority
GB
United Kingdom
Prior art keywords
acid
chloromethylthiazole
thiazoles
benzimidazole
thiazolyl
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
GB35141/62A
Inventor
Janos Kollonitsch
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1020034A publication Critical patent/GB1020034A/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
    • C07D277/02—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
    • C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Chloroalkyl thiazoles are prepared by treating C1- 6 alkyl thiazoles with atomic chlorine in a reaction medium comprising sulphuric acid, fuming sulphuric acid, chlorosulphonic acid, pyrosulphuric acid or a mixture of two or more of such materials, at least one mole of the acid being present per mole of alkyl thiazole compound. The atomic chlorine is preferably produced in situ in the mixture by irradiating the reaction mass or by using a chemical freeradical initiator. A halide of P, As or Sb is preferably also present. The invention also comprises the compound 2-chloromethylthiazole. The chloralkyl thiazoles may be hydrolysed to the corresponding carbinols which may be oxidized to the corresponding carboxylic acids and then esterified or converted to derivatives such as amides, aldehydes and acid halides. Examples are given. Example 1 describes the hexamine salt of 4-chloromethylthiazole. Example 7 describes the reaction sequence 4 - chloromethylthiazole --> 4-acetoxymethylthiazole --> 4 - hydroxymethylthiazole --> copper salt of thiazole - 4 - carboxylic acid --> the free acid --> the acid chloride --> thiazole - 4 - carboxylic acid onitroanilide --> 2 - (41 - thiazolyl) - benzimidazole. In a similar manner 2-chloromethylthiazole and 5 - chloromethylthiazole are converted respectively to 2 - (21 - thiazolyl) - benzimidazole and 2 - (51 - thiazolyl) - benzimidazole.
GB35141/62A 1961-06-16 1962-09-14 Chloroalkyl thiazoles Expired GB1020034A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US11752361A 1961-06-16 1961-06-16

Publications (1)

Publication Number Publication Date
GB1020034A true GB1020034A (en) 1966-02-16

Family

ID=38983792

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35141/62A Expired GB1020034A (en) 1961-06-16 1962-09-14 Chloroalkyl thiazoles

Country Status (6)

Country Link
BE (1) BE623148A (en)
CH (1) CH429732A (en)
FR (1) FR1514062A (en)
GB (1) GB1020034A (en)
NL (1) NL284180A (en)
SE (1) SE303749B (en)

Also Published As

Publication number Publication date
BE623148A (en) 1963-04-03
FR1514062A (en) 1968-02-23
CH429732A (en) 1967-02-15
NL284180A (en) 1965-01-11
SE303749B (en) 1968-09-09

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