Diethyl Oxalate → HCID 178470315, Verbindung

HRID 131203

Reaktionsgleichung

Reaktionsgleichung von HRID 131203
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH2:9])=[O:8].CC[O-].[Na+].[CH2:14]([O:16][C:17](=[O:23])[C:18](OCC)=O)[CH3:15]>CCO>[OH:8][C:7]1[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[N:1]=[C:18]([C:17]([O:16][CH2:14][CH3:15])=[O:23])[N:9]=1

Komponenten

5

Edukt 3

HCID 7268Diethyl OxalateHCID 5189933-Aminothiophene-2-carboxamideHCID 2723922Sodium ethoxide

Produkt 1

HCID 178470315HCID 178470315, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-aminothiophene-2-carboxamide (1.23 g, 8.65 mmol) and EtOH (25 mL) was treated with NaOEt (1.2 g, 17.3 mmol) and diethyloxalate (2.3 mL, 17.3 mmol), refluxed for 18 h, cooled, concentrated in vacuo, treated with water, acidified with HOAc and filtered to give the title compound (1.43 g, 74%) as a cream solid: IR νmax Nujol)/cm−1 3180, 3119, 3078, 3006, 2955, 2924, 2854, 1737, 1667, 1651, 1300 and 1176; NMR δH (400 MHz, DMSO) 1.37 (3H, t, J 7.0 Hz), 4.40 (2H, q, J 7.0 Hz), 7.58 (1H, d, J 5.0 Hz), 8.30 (1H, d, J 5.1 Hz), and 12.92 (1H, s).

Aufarbeitung

  1. temperaturerefluxed for 18 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. additiontreated with water
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-18e76db551d84be996568917ff3e1d18
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384949B2

Verknüpfte Notizen

Wird geladen…