DE109345C - - Google Patents
Info
- Publication number
- DE109345C DE109345C DENDAT109345D DE109345DA DE109345C DE 109345 C DE109345 C DE 109345C DE NDAT109345 D DENDAT109345 D DE NDAT109345D DE 109345D A DE109345D A DE 109345DA DE 109345 C DE109345 C DE 109345C
- Authority
- DE
- Germany
- Prior art keywords
- chj
- tetramethylpyrroline
- carboxamide
- methyl
- base
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetone amine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VDVJQFLGCFFFBP-UHFFFAOYSA-N 2,3-dihydropyrrole-1-carboxylic acid Chemical compound OC(=O)N1CCC=C1 VDVJQFLGCFFFBP-UHFFFAOYSA-N 0.000 description 1
- BSKZDJXVMPWPRA-UHFFFAOYSA-N O.[Br] Chemical compound O.[Br] BSKZDJXVMPWPRA-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Trioxopurine Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- 229940116269 Uric Acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
UWVUWV
Durch Behandlung von Triacetonamin mit Brom in stark bromwasserstoffsaurer Lösung erhält man, wie Berichte d. d. ehem. Ges. XXXI, 668, gezeigt wurde, das Bromhydrat eines Dibromtriacetonamins. Letzteres tauscht beim Digeriren mit Ammoniak seine beiden im Kern sitzenden Bromatome gegen die N H- GruppeBy treating triacetonamine with bromine in a strongly hydrobromic acid solution, as has been shown in reports from the former Ges. XXXI, 668, the bromine hydrate of a dibromotriacetonamine is obtained. The latter replaces the digesting with ammonia his two seated in the core bromine against the N H group
COCO
aus unter Bildung einer Base C9 H16 N2 O, welcher der Name Iminotriacetonamin gegeben wurde. Wie die nähere Untersuchung letzteren Körpers gezeigt hat, enthält er jedoch nicht mehr den Ring des Triacetonamins, sondern ist vielmehr das Amid einer Pyrrolincarbonsäure, das sich nach folgender Gleichung bildet:from forming a base C 9 H 16 N 2 O, which was given the name iminotriacetonamine. As the closer examination of the latter has shown, however, it no longer contains the ring of triacetonamine, but is rather the amide of a pyrroline carboxylic acid, which is formed according to the following equation:
COCO
(CH3J2C(CH 3 J 2 C
C(CHJ2 C (CHJ 2
(CHJ2C C(CHJ2 (CHJ 2 CC (CHJ 2
NHNH
CH=^C-CO-NH2 CH = ^ C-CO-NH 2
I II I
(CHJ2C C(CHJ2 (CHJ 2 CC (CHJ 2
NHNH
NHNH
a-Tetramethylpyrrolin-ß-carbonsäureamid.α-Tetramethylpyrroline-β-carboxamide.
Es wurde nun gefunden, dafs man durch Einwirkung von Halogenalkylen, wie Jodmethyl und dergl., auf diese Base Alkylderivate herstellen kann. Die Base nimmt dabei eine Alkylgruppe auf, welche an das 2V-Atom im Pyrrolring eintritt.It has now been found that the action of haloalkylenes, such as iodomethyl and the like. Can produce alkyl derivatives on this base. The base takes one Alkyl group, which occurs at the 2V atom in the pyrrole ring.
CH=C-CO-NHCH = C-CO-NH
(CHJ2C(CHJ 2 C
I
C(CHJ2 I.
C (CHJ 2
+ CH3J =+ CH 3 J =
CH--CH--
(CHJ2C(CHJ 2 C
=C-C0-NH2 = C-CO-NH 2
C(CHJ2 C (CHJ 2
NHNH
N-CH-HJN-CH-HJ
!-TetramethylpyrrolinjS-carbonsäureamid. ! -TetramethylpyrrolinjS-carboxamide.
N-Methyl-a-tetramethylpyrroIin-/3-carbonsäureamid. N-methyl-a-tetramethylpyrroline / 3-carboxamide.
ι Th. a-Tetramethylpyrrolin-ß-carbonsä'ureafnid wird mit ι Th. Jodmethyl und 3 Th. Methylalkohol 5 bis 12 Tage lang stehen gelassen. Alsdann wird der Methylalkohol abdestillirt, der ölige Rückstand mit etwas Wasser aufgenommen und das N-Methyl -a-Tetramethylpyrrolin-ß-carbonsäureamid durch festes Alkali abgeschieden. Die neue Base ist leicht löslich in Aether, Aceton, Alkohol, Benzol und Wasser. Aus Ligrom krystallisirt, bildet sie rautenförmige Tafeln und Schuppen, Schmp. 1040.ι Th. α-Tetramethylpyrroline-ß-carboxylic acid acid is left with ι Th. Iodomethyl and 3 Th. Methyl alcohol for 5 to 12 days. The methyl alcohol is then distilled off, the oily residue is taken up with a little water and the N- methyl-α-tetramethylpyrroline-β-carboxamide is separated off by solid alkali. The new base is easily soluble in ether, acetone, alcohol, benzene and water. Crystallized from ligrom, it forms diamond-shaped tablets and scales, m.p. 104 0 .
In ähnlicher Weise vollzieht sich das Verfahren, wenn an Stelle der Methylgruppe andere Alkylgruppen eingeführt werden.The process is carried out in a similar manner if the methyl group is replaced by others Alkyl groups are introduced.
Die nach vorstehend beschriebenem Verfahren entstehenden n-Alkylderivate sollen zu pharmaceutischen Zwecken Verwendung finden, da sie befähigt sind, mit der Harnsäure leicht lösliche Salze zu bilden. The n- alkyl derivatives formed by the process described above are intended to be used for pharmaceutical purposes, since they are capable of forming readily soluble salts with uric acid.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE109345C true DE109345C (en) |
Family
ID=379252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT109345D Active DE109345C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE109345C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4703056A (en) * | 1983-01-21 | 1987-10-27 | Alkaloida Vegyeszeti Gyar | New alkyl diamine derivatives |
| US4731376A (en) * | 1983-01-20 | 1988-03-15 | Alkaloida Vegyeszeti Gyar | 2-(-(2,2,5,5-tetramethyl-3-pyrrolin-3-carbonyl))-amino derivatives |
-
0
- DE DENDAT109345D patent/DE109345C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731376A (en) * | 1983-01-20 | 1988-03-15 | Alkaloida Vegyeszeti Gyar | 2-(-(2,2,5,5-tetramethyl-3-pyrrolin-3-carbonyl))-amino derivatives |
| US4703056A (en) * | 1983-01-21 | 1987-10-27 | Alkaloida Vegyeszeti Gyar | New alkyl diamine derivatives |
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