Ethyl 3-ethoxy-3-iminopropionate hydrochloride → HCID 178471908, Verbindung

HRID 1875378

Reaktionsgleichung

Reaktionsgleichung von HRID 1875378
Cl.[CH2:2]([O:4][C:5](=[NH:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3].[Br:13][C:14]1[CH:20]=[CH:19][C:17](N)=[CH:16][C:15]=1[O:21][CH3:22]>CCO>[Br:13][C:14]1[CH:20]=[CH:19][C:17](/[N:12]=[C:5](/[O:4][CH2:2][CH3:3])\[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:16][C:15]=1[O:21][CH3:22]

Komponenten

4

Edukt 2

HCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 70182544-Bromo-3-methoxyaniline

Produkt 1

HCID 178471908HCID 178471908, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

A mixture of ethyl 3-ethoxy-3-iminopropanoate hydrochloride (54.2 g, 277 mmol) and 4-bromo-3-methoxyaniline (56.0 g, 277 mmol) in EtOH (500 mL) was stirred under nitrogen, at 22° C., for 20 hours. The mixture was filtered and concentrated, then stirred in ether (100 mL), filtered and concentrated. The residue was chromatographed on silica gel 60 (gradient elution, 0-50% EtOAc in hexane) to give the title product. 1H NMR (400 MHz, CDCl3) δ 7.40 (d, J=8.4 Hz, 1H); 6.43 (d, J=2.0 Hz, 1H); 6.30 (dd, J=8.4 & 2.4 Hz, 1H); 4.28 (q, J=7.1 Hz, 2H); 4.15 (q, J=7.1 Hz, 2H); 3.85 (s, 2H); 3.21 (s, 2H); 1.34 (t, J=7.2 Hz, 3H); 1.26 (t, J=7.0 Hz, 3H) ppm. LRMS (ESI) m/z 344.0 [(M+H)+; calcd for C14H19BrNO4: 344.0].

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. stirringstirred in ether (100 mL)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel 60 (gradient elution, 0-50% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-16eeb4f42cc74faf877fe533a051248a
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309540B2

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