GB667116A - Manufacture of biguanide derivatives - Google Patents

Manufacture of biguanide derivatives

Info

Publication number
GB667116A
GB667116A GB1092049A GB1092049A GB667116A GB 667116 A GB667116 A GB 667116A GB 1092049 A GB1092049 A GB 1092049A GB 1092049 A GB1092049 A GB 1092049A GB 667116 A GB667116 A GB 667116A
Authority
GB
United Kingdom
Prior art keywords
hydrochloride
alkyl radicals
hydrobromide
carbon atoms
formula
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
GB1092049A
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.)
MURIEL RUTH CURD
Imperial Chemical Industries Ltd
Original Assignee
MURIEL RUTH CURD
Imperial Chemical Industries Ltd
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 MURIEL RUTH CURD, Imperial Chemical Industries Ltd filed Critical MURIEL RUTH CURD
Priority to GB1092049A priority Critical patent/GB667116A/en
Publication of GB667116A publication Critical patent/GB667116A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C07C279/26—X and Y being nitrogen atoms, i.e. biguanides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Biguanide derivatives of the general formula <FORM:0667116/IV (b)/1> (wherein R and R1 represent hydrogen or alkyl radicals of 1-5 carbon atoms, R11 and R111 represent hydrogen or alkyl radicals such that together they contain 2-7 carbon atoms, and of X, Y and Z, at least one represents Cl, Br or I and the others H, Cl, Br, I or alkyl radicals of 1-5 carbon atoms) are manufactured by interaction of a guanidine derivative of the formula <FORM:0667116/IV (b)/2> in the form of a salt thereof with an S-alkylisothiourea of the formula <FORM:0667116/IV (b)/3> (wherein Alkyl includes aromatic substituted alkyl radicals) in the presence of an alkali metal alkoxide in a non-hydroxylic liquid organic medium of boiling point above 100 DEG C. In examples, the following compounds are refluxed in toluene in the presence of sodium methoxide: (1) p-chlorophenylguanidine hydrochloride and S - ethyl - N - isopropylisothiourea hydrobromide; (2) 3 : 4 - dichlorophenylguanidine hydrochloride and S-benzyl-N-isopropylisothiourea hydrochloride; (3) p-chlorophenylguanidine hydrochloride and N : N : S-triethylisothiourea hydrobromide. Specifications 603,070, 607,720 and 624,578 are referred to. 3 : 4 - Dichlorophenylguanidine is obtainable by condensing 3 : 4-dichloraniline hydrochloride with benzoylcyanamide in ethanol and hydrolysing the product with aqueous caustic soda. N : N : S - Triethylisothiourea hydrobromide is obtainable by reacting N : N-diethylthiourea with ethyl bromide.
GB1092049A 1949-04-25 1949-04-25 Manufacture of biguanide derivatives Expired GB667116A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1092049A GB667116A (en) 1949-04-25 1949-04-25 Manufacture of biguanide derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1092049A GB667116A (en) 1949-04-25 1949-04-25 Manufacture of biguanide derivatives

Publications (1)

Publication Number Publication Date
GB667116A true GB667116A (en) 1952-02-27

Family

ID=9976723

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1092049A Expired GB667116A (en) 1949-04-25 1949-04-25 Manufacture of biguanide derivatives

Country Status (1)

Country Link
GB (1) GB667116A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011342A (en) * 1971-06-02 1977-03-08 Seperic Method and composition for the treatment of hypertension with ortho-disubstituted arylguanidines
US5322858A (en) * 1992-02-14 1994-06-21 Jacobus Pharmaceutical Co. Inc. N,N'-substituted imidodicarbonimidic diamides derived from hydroxylamines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011342A (en) * 1971-06-02 1977-03-08 Seperic Method and composition for the treatment of hypertension with ortho-disubstituted arylguanidines
US5322858A (en) * 1992-02-14 1994-06-21 Jacobus Pharmaceutical Co. Inc. N,N'-substituted imidodicarbonimidic diamides derived from hydroxylamines

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