DE514248C - Verfahren zur Darstellung substituierter Guanidine - Google Patents
Verfahren zur Darstellung substituierter GuanidineInfo
- Publication number
- DE514248C DE514248C DEC40409D DEC0040409D DE514248C DE 514248 C DE514248 C DE 514248C DE C40409 D DEC40409 D DE C40409D DE C0040409 D DEC0040409 D DE C0040409D DE 514248 C DE514248 C DE 514248C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- preparation
- substituted guanidines
- chlorohydrate
- aniline
- 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
- 150000002357 guanidines Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 amine salt Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001912 cyanamides Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 229940075930 picrate Drugs 0.000 description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 4
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- JBCSOBKDUKAJHR-UHFFFAOYSA-N ClO.NC1=CC=CC=C1 Chemical compound ClO.NC1=CC=CC=C1 JBCSOBKDUKAJHR-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- ZZTSQZQUWBFTAT-UHFFFAOYSA-N diethylcyanamide Chemical compound CCN(CC)C#N ZZTSQZQUWBFTAT-UHFFFAOYSA-N 0.000 description 2
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- HPOVMERCXHNITA-UHFFFAOYSA-N 1,1-diethyl-2-phenylguanidine Chemical compound CCN(CC)C(=N)NC1=CC=CC=C1 HPOVMERCXHNITA-UHFFFAOYSA-N 0.000 description 1
- ZBNUSTIRUCARLG-UHFFFAOYSA-N 1,1-dimethyl-2-(3-methylbutyl)guanidine Chemical compound CC(C)CCNC(=N)N(C)C ZBNUSTIRUCARLG-UHFFFAOYSA-N 0.000 description 1
- RGDAQOCIEGWPFM-UHFFFAOYSA-N ClO.CCN Chemical compound ClO.CCN RGDAQOCIEGWPFM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- NWJGNHCFEPMCCT-UHFFFAOYSA-N diphenylcyanamide Chemical compound C=1C=CC=CC=1N(C#N)C1=CC=CC=C1 NWJGNHCFEPMCCT-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
- Verfahren zur Darstellung substituierter Guanidine Während Cyanamid und Monoalkylcyanamide sehr bequem mit Aminsalzen reagieren, insbesondere wenn man in sehr konzentrierter Lösung arbeitet, wie dies in der Patentschrift 512 88o angeführt wurde, reagieren disubstituierte Cyanamide mit Aminen oder Aminsalzen nicht (vgl. L e c h e r und D e m m 1 e r, Zeitschrift für physiologische Chemie, Bd. 167 [i927], S. 17o).
- Es wurde nun gefunden, daß Dialkylcyanamide dann sehr leicht mit Aminsalzen reagieren, wenn man sie in Gegenwart von freien Aminen zusammenbringt. Bei manchen Derivaten ist es dabei nicht einmal nötig, die Temperatur zu erhöhen. Der Grund dieser eigenartigen Reaktion ist noch nicht sicher aufgeklärt, möglicherweise entsteht ein Zwischenprodukt folgender Konstitution das mit dem Amin weiterreagiert. Beispiel i 5 Teile Diäthylcyanamid mit 6,5 Teilen Anilinchlorhydrat und 3 Teilen Anilin i o Stunden auf i oo° erhitzt, geben das N, N-Diäthyl-N'-phenylguanidin, das als ölige Base durch Wasserdampfdestillation des alkalisierten Ansatzes gewonnen wird oder, als Pikrat vom Schmelzpunkt i 18° abgeschieden werden kann. Anilin reagiert übrigens auch ohne Chlorhydratzusatz mit dem Dialkylcyanamid; die Ausbeuten an Guanidin sind jedoch in ersterem Falle günstiger.
- Beispiele 2,7 Teile Diäthylcyanamid, 5 Teile Isoamylainin und 7 Teile Isoamylaminchlorhydrat geben beim längeren Stehen oder bei etwa. istündigem Erhitzen auf ioo° das N,N-Diäfhyl-N'-isoamylguanidin, dessen Halogenwasserstoffsalze leicht wasserlöslich sind Lind dessen Pikrat bei i2o° schmilzt.
- Beispiel 3 3 Teile Dimethylcyariarnid auf die gleiche Weise wie in Beispiele behandelt (q. Teile Amin, 5 Teile C'hlorhydrat), geben das N,N-Dimet'hyl - N' - isoamylguanidin. Das Pikrat schmilzt bei 1o4°.
- Beispiel q.
- 2 Teile Dimethylcyanamid, 1,9 Teile @thvlamin, 3,5 Teile Äthylaminchlorhydrat geben nach einigem Stehen das N, N-Dimethyl-N'-äthyIguanidin; Pikrat: Schmelzpunkt 152°. Beispiel 5 2o g Diphenylcyanamid werden in Gegenwart von wenig Alkohol b Stunden mit 1 o g Anilin und 13 g Anilinchlorhydrat erhitzt. Aus dem Reaktionsprodukt läßt sich das Triphenviguanidin vom Schmelzpunkt 133° in sehr guter Ausbeute isolieren.
Claims (1)
- PATENTANSPRUCH: Verfahren zur Darstellung substituierter Guanidine, dadurch gekennzeichnet, daß man disubstituierte Cyanämide mit einer Mischung von Amin und Aminsalz behandelt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC40409D DE514248C (de) | 1927-09-13 | 1927-09-13 | Verfahren zur Darstellung substituierter Guanidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC40409D DE514248C (de) | 1927-09-13 | 1927-09-13 | Verfahren zur Darstellung substituierter Guanidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE514248C true DE514248C (de) | 1930-12-10 |
Family
ID=7024161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC40409D Expired DE514248C (de) | 1927-09-13 | 1927-09-13 | Verfahren zur Darstellung substituierter Guanidine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE514248C (de) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0517852A4 (de) * | 1990-03-02 | 1994-03-02 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of | |
| 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 |
| 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 |
| 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 |
| US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US5922772A (en) * | 1993-11-23 | 1999-07-13 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6147063A (en) * | 1993-05-27 | 2000-11-14 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6174924B1 (en) | 1994-02-03 | 2001-01-16 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
-
1927
- 1927-09-13 DE DEC40409D patent/DE514248C/de not_active Expired
Cited By (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| US5637622A (en) * | 1990-03-02 | 1997-06-10 | 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 |
| 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 |
| US6251948B1 (en) | 1990-03-02 | 2001-06-26 | 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 | 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 |
| US5798390A (en) * | 1990-03-02 | 1998-08-25 | 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 |
| US5767162A (en) * | 1990-03-02 | 1998-06-16 | 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 |
| EP0517852A4 (de) * | 1990-03-02 | 1994-03-02 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of | |
| 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 |
| US5686495A (en) * | 1991-02-08 | 1997-11-11 | Cambridge Neuroscience, Inc. | Substituted hydrazinedicarboximidamides and methods of use thereof |
| US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5670519A (en) * | 1991-02-08 | 1997-09-23 | Cambridge Neuroscience, Inc. | Acenaphthyl-substituted guanidines and methods of use thereof |
| US5672608A (en) * | 1991-02-08 | 1997-09-30 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5677348A (en) * | 1991-02-08 | 1997-10-14 | Cambridge Neuroscience, Inc. | Substituted aminoguanidines and methods of use thereof |
| US5681861A (en) * | 1991-02-08 | 1997-10-28 | Cambridge Neuroscience, Inc. | Aminoguanidines and methods of use of same |
| US5637623A (en) * | 1991-02-08 | 1997-06-10 | Cambridge Neuroscience, Inc. | Substituted adamantyl guanidines and methods of use there of |
| US6071969A (en) * | 1991-02-08 | 2000-06-06 | Cambridge Neuroscience, Inc. | Substituted aminoguanidines and methods of use thereof |
| US5622968A (en) * | 1991-02-08 | 1997-04-22 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5614630A (en) * | 1991-02-08 | 1997-03-25 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5837737A (en) * | 1991-02-08 | 1998-11-17 | Cambridge Neuroscience, Inc. | Hydrazinedicarboximidamide compounds and pharmaceutical composition comprising same |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| 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 |
| US5652269A (en) * | 1991-02-08 | 1997-07-29 | Cambridge Neuroscience, Inc. | Substituted hydrazinecarboximidamides and methods of use thereof |
| US6153604A (en) * | 1993-05-27 | 2000-11-28 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6147063A (en) * | 1993-05-27 | 2000-11-14 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US5955507A (en) * | 1993-11-23 | 1999-09-21 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6013675A (en) * | 1993-11-23 | 2000-01-11 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6156741A (en) * | 1993-11-23 | 2000-12-05 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US5922772A (en) * | 1993-11-23 | 1999-07-13 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6174924B1 (en) | 1994-02-03 | 2001-01-16 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6288123B1 (en) | 1994-02-03 | 2001-09-11 | Cambridge Neurosciences, Inc. | Therapeutic guanidines |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
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