Hydrochloric Acid → ethyl 1-(2-ethoxy-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate hydrochloride

HRID 77364

Reaktionsgleichung

Reaktionsgleichung von HRID 77364
[C:1]([CH2:3][N:4]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:2].[ClH:15].[CH2:16]([O:18]CC)[CH3:17].C(O)C>>[ClH:15].[CH2:16]([O:18][C:1](=[NH:2])[CH2:3][N:4]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:17]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 86706662ethyl 1-(cyanomethyl)-5-methyl-1H-pyrrole-2-carboxylate

Produkt 1

HCID 86706663ethyl 1-(2-ethoxy-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate hydrochlorideAusbeute 95,7 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A high pressure reaction vessel charged with ethyl 1-(cyanomethyl)-5-methyl-1H-pyrrole-2-carboxylate (848 mg, 4.41 mmol) cooled to 0° C. was treated with a 2M solution of hydrochloric acid in diethyl ether (30 mL, 60 mmol) and absolute ethanol (406 mg, 8.82 mmol). The mixture was stirred at 0° C. for 10 min and then was warmed to room temperature where it stirred over the weekend. At this time, the mixture was diluted with hexanes. The resulting precipitate was collected by filtration to afford ethyl 1-(2-ethoxy-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate hydrochloride (1.16 g, 95.7%) as a white solid. LC-MS calcd. for C12H19N2O3 [(M+H)+] 239, obsd. 239.0.

Aufarbeitung

  1. customA high pressure reaction vessel
  2. temperaturewas warmed to room temperature where it
  3. stirringstirred over the weekend
  4. filtrationThe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-74d36ae72802488f9990d44583f7963c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841299B2

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