US1795738A - Method of producing substituted guanidines - Google Patents
Method of producing substituted guanidines Download PDFInfo
- Publication number
- US1795738A US1795738A US305863A US30586328A US1795738A US 1795738 A US1795738 A US 1795738A US 305863 A US305863 A US 305863A US 30586328 A US30586328 A US 30586328A US 1795738 A US1795738 A US 1795738A
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- US
- United States
- Prior art keywords
- producing substituted
- substituted guanidines
- amine
- parts
- alpha
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- 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.)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
Definitions
- My invention refers to the production of guanidine derivatives and more especially to a method of producing substituted guan1- dines.
- tween dialkyl cyanamides and amine salts is caused to take place very smoothly, and with many derivatives it is not even necessary to increase the temperature.
- the process of manufacture accordingto the invention is by bringing a dialkyl cyanamide into reaction with an amine salt in the presence of a free amine.
- hydrohalogen acid salts of which are easily soluble in water and the picrate of;
- Example 4 The method of producing substituted guanidines by treating a dialkyl cyanamid with a salt of an amine which has at least one hydrogen atom attached to the nitrogen atom, in the presence of the corresponding free amine.
- Example 1 5 parts of diethyl cyanamide heated with i 6.5 parts of aniline hydrochloride and 3 parts of aniline for 10 hours to 100 C. give alpha, alpha-diethyl-beta-phenyl guanidine which is obtained as the oily base by steam distillation of the deposit after rendering alkaline or which can be separated as the pi'crate of melt-
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Mar. ie, 1931 omrsn stares rarer 'FFICE HERBERT scnorrnon nnnmn-nnrnrcxnnnonr, GERMANY, ASSIGNOR 'IO scnnnmo- 1 KAI-ILBAUM A. a, or BERLIN, GERMANY METHOI P OF PRODUCING SUBSTITUTED GUANIDINES No Drawing. Application filed September 13, 1928, Serial No. 305,863, and in Germany September 12, 1927.
My invention refers to the production of guanidine derivatives and more especially to a method of producing substituted guan1- dines. I i
l/Vhereas cyanamide and mono alkyl cyanamides react with amine salts veryf'avourably particularly when working in Very concentrated solution disubstituted cyanamides do not'react favourably with amines or amine salts. (Compare Lecher & Demmler Zeitschrift fur physiologische Chemie 167,170 (1927)). v
' By the present invention the reaction be-,
tween dialkyl cyanamides and amine salts is caused to take place very smoothly, and with many derivatives it is not even necessary to increase the temperature.
The process of manufacture accordingto the invention is by bringing a dialkyl cyanamide into reaction with an amine salt in the presence of a free amine.
The reason for the smooth and favourable reaction cannot yet be, definitely explained, possibly an intermediate product of the following constitution is produced R R \N/ ({X [I NH wherein R is an alkyl and X an acid radical which reacts further with the amine.
The following formula shows the structure of the guanidine nucleus,
are however better in the first case.
ing point 118 C. Aniline itself also reacts with dialkyl cyanamide without the addition of hydrochloride. The yields of guanidine Example 2 2.7 parts of diethyl cyanamide, 5 parts of isoamylamine and 7 parts of isoamylamine hydrochloride give on long standing or after heating for about one hour to 100 C. the alpha, alpha-dlethyLbeta-isoamyl guanidine,
the hydrohalogen acid salts of which are easily soluble in water and the picrate of;
the same manner as in Example 2 (with four parts of amine and live partsof hydrochloride) give alpha alpha-dimethyl-beta-iso-,
The. picrate melts at.
amyl-guanidine Example 4 The method of producing substituted guanidines by treating a dialkyl cyanamid with a salt of an amine which has at least one hydrogen atom attached to the nitrogen atom, in the presence of the corresponding free amine.
HERBERT SCHOTTE.
N511 6 NHfY The following examples illustrate the invention.
' Example 1 5 parts of diethyl cyanamide heated with i 6.5 parts of aniline hydrochloride and 3 parts of aniline for 10 hours to 100 C. give alpha, alpha-diethyl-beta-phenyl guanidine which is obtained as the oily base by steam distillation of the deposit after rendering alkaline or which can be separated as the pi'crate of melt-
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1795738X | 1927-09-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
US1795738A true US1795738A (en) | 1931-03-10 |
Family
ID=7743656
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US305863A Expired - Lifetime US1795738A (en) | 1927-09-12 | 1928-09-13 | Method of producing substituted guanidines |
Country Status (1)
Country | Link |
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US (1) | US1795738A (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2425341A (en) * | 1944-08-11 | 1947-08-12 | American Cyanamid Co | Production of mono- and unsymmetrically disubstituted guanidines |
US2446421A (en) * | 1944-11-03 | 1948-08-03 | Ici Ltd | Manufacture of arylbiguanide hydrochlorides |
US2537834A (en) * | 1951-01-09 | Substituted guanylmelamines | ||
US2898369A (en) * | 1956-02-23 | 1959-08-04 | Mcneilab Inc | N,n,n',n'' tetraethyl guanidine and its acid addition salts |
US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5336689A (en) * | 1990-03-02 | 1994-08-09 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5385946A (en) * | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
US5403861A (en) * | 1991-02-08 | 1995-04-04 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
US5574070A (en) * | 1990-05-25 | 1996-11-12 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US6072075A (en) * | 1997-05-22 | 2000-06-06 | The Regents Of The University Of California | Guanidinylation reagents |
US20070265348A1 (en) * | 1994-02-03 | 2007-11-15 | Scion Pharmaceuticals, Inc, A Delaware Corporation | Therapeutic guanidines |
US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
-
1928
- 1928-09-13 US US305863A patent/US1795738A/en not_active Expired - Lifetime
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2537834A (en) * | 1951-01-09 | Substituted guanylmelamines | ||
US2425341A (en) * | 1944-08-11 | 1947-08-12 | American Cyanamid Co | Production of mono- and unsymmetrically disubstituted guanidines |
US2446421A (en) * | 1944-11-03 | 1948-08-03 | Ici Ltd | Manufacture of arylbiguanide hydrochlorides |
US2898369A (en) * | 1956-02-23 | 1959-08-04 | Mcneilab Inc | N,n,n',n'' tetraethyl guanidine and its acid addition salts |
US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5385946A (en) * | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
US5604228A (en) * | 1986-07-10 | 1997-02-18 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5478863A (en) * | 1986-07-10 | 1995-12-26 | State Of Oregon, Oregon Health Sciences University Of Oregon | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5502255A (en) * | 1986-07-10 | 1996-03-26 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5336689A (en) * | 1990-03-02 | 1994-08-09 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5559154A (en) * | 1990-03-02 | 1996-09-24 | Oregon State Board Of Higher Education | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5574070A (en) * | 1990-05-25 | 1996-11-12 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5403861A (en) * | 1991-02-08 | 1995-04-04 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
US5672608A (en) * | 1991-02-08 | 1997-09-30 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
US20070265348A1 (en) * | 1994-02-03 | 2007-11-15 | Scion Pharmaceuticals, Inc, A Delaware Corporation | Therapeutic guanidines |
US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
US6072075A (en) * | 1997-05-22 | 2000-06-06 | The Regents Of The University Of California | Guanidinylation reagents |
US6380358B1 (en) | 1997-05-22 | 2002-04-30 | The Regents Of The University Of California | Guanidinylation reagents |
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