Ethanolamine → Methyl 3-chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate

HRID 1874964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874964
[CH2:1]([CH2:3][NH2:4])[OH:2].[Cl:5][C:6]1[CH:10]=[C:9]([C:11](Cl)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[Cl:5][C:6]1[CH:10]=[C:9]([C:11]([NH:4][CH2:3][CH2:1][OH:2])=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 68487232Methyl 3-chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylateAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethanolamine (0.175 mL, 2.90 mmol) was added to a solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.150 g, 0.580 mmol) in THF and the resulting solution stirred until no starting material was evident by TLC. Purification was accomplished by silica gel column chromatography (30-100% EtOAc/hexanes) to afford the title compound (0.082 g, 57%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.37 (br. s., 1H), 8.42 (t, 1H), 6.80 (s, 1H), 4.75 (t, 1H), 3.78 (s, 3H), 3.46 (q, 2H), 3.27 (q, 2H). LCMS: m/z 245.4 (M−1).

Aufarbeitung

  1. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-20e73671c981424ea5001ff02cbebfd3
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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