GB585834A - Alkamine esters of pyrrole substituted acrylic acids - Google Patents
Alkamine esters of pyrrole substituted acrylic acidsInfo
- Publication number
- GB585834A GB585834A GB12005/44A GB1200544A GB585834A GB 585834 A GB585834 A GB 585834A GB 12005/44 A GB12005/44 A GB 12005/44A GB 1200544 A GB1200544 A GB 1200544A GB 585834 A GB585834 A GB 585834A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimethylpyrrole
- prepared
- pyrrole
- alkyl
- esters
- 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
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 150000001253 acrylic acids Chemical class 0.000 title 1
- 125000000168 pyrrolyl group Chemical group 0.000 title 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 4
- 239000002585 base Substances 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 dialkylamino alcohol Chemical compound 0.000 abstract 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 abstract 2
- XFQXNCWPENNOBZ-UHFFFAOYSA-N 1-amino-2-ethylbutan-1-ol Chemical compound CCC(CC)C(N)O XFQXNCWPENNOBZ-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000012190 activator Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 abstract 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two double bonds between ring members or between ring members and non-ring members 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)
- Pyrrole Compounds (AREA)
Abstract
Alkamine esters of 1 : 2 : 4-trimethylpyrrole-5-carboxylic acid-3-acrylic acid of the general formula <FORM:0585834/IV/1> where X is a dialkylaminoalkyl radical, are prepared by heating the corresponding alkyl ester with the desired dialkylamino alcohol in the presence of an alkali metal alcoholate. The starting materials for the present invention are preferably obtained by the reaction of pyrrole aldehydes with an alkyl acid malonate in the presence of a base such as piperidine. In examples: (1) diethyl-1 : 2 : 4-trimethylpyrrole-5-carboxylate-3-b -acrylate is refluxed with b -diethylaminoethanol in the presence of sodium; (2) as in example (1) except that b -diethylaminopropanol is used as the alcohol. The compounds of the invention are used in the form of their hydrochlorides as local an sthetics and in the form of the free bases as activators for rubber accelerators. The parent alkyl esters are prepared by reacting the pyrrole aldehyde with an alkyl acid malonate in the presence of a base such as piperidine. The pyrrole aldehyde is prepared by the action of zinc cyanide and hydrogen chloride at low temperature on ethyl 1 : 2 : 4-trimethylpyrrole-5-carboxylate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US585834XA | 1943-07-31 | 1943-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB585834A true GB585834A (en) | 1947-02-26 |
Family
ID=22017730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12005/44A Expired GB585834A (en) | 1943-07-31 | 1944-06-23 | Alkamine esters of pyrrole substituted acrylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB585834A (en) |
-
1944
- 1944-06-23 GB GB12005/44A patent/GB585834A/en not_active Expired
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