GB667116A - Manufacture of biguanide derivatives - Google Patents
Manufacture of biguanide derivativesInfo
- 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
Links
- 150000004283 biguanides Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- RMFZXBDENVVLSL-UHFFFAOYSA-N 2-(4-chlorophenyl)guanidine;hydrochloride Chemical compound Cl.NC(N)=NC1=CC=C(Cl)C=C1 RMFZXBDENVVLSL-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal alkoxide Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- HXJSCQPQMWOXLQ-UHFFFAOYSA-N benzyl N'-propan-2-ylcarbamimidothioate hydrochloride Chemical compound Cl.C(C1=CC=CC=C1)SC(NC(C)C)=N HXJSCQPQMWOXLQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HMDYXMGGYFYARX-UHFFFAOYSA-N ethyl N'-propan-2-ylcarbamimidothioate hydrobromide Chemical compound Br.C(C)SC(NC(C)C)=N HMDYXMGGYFYARX-UHFFFAOYSA-N 0.000 abstract 1
- 150000002357 guanidines Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- DBFAKALHTSOYSG-UHFFFAOYSA-N n-cyanobenzamide Chemical compound N#CNC(=O)C1=CC=CC=C1 DBFAKALHTSOYSG-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (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.
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)
| 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 |
-
1949
- 1949-04-25 GB GB1092049A patent/GB667116A/en not_active Expired
Cited By (2)
| 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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