Trifluoroacetic acid → HCID 66626031, Verbindung

HRID 1663268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1663268
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([NH2:16])[S:8][C:7]=1[NH2:17])=[O:5])[CH3:2].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]=O.FC(F)(F)C(O)=O>C(O)(C)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([N:16]=[CH:23][C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)[S:8][C:7]=1[NH2:17])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 73642-ThiophenecarboxaldehydeHCID 840025Diethyl 2,5-diaminothiophene-3,4-dicarboxylate

Produkt 1

HCID 66626031HCID 66626031, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

In a round bottom flask (50 mL), 2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester (50 mg) was added to 20 mL isopropanol to which was added 2-thiophenecarboxaldehyde (24 mg) and a catalytic amount of trifluoroacetic acid (TFA). The mixture was refluxed for 20 hours. Complete removal of the solvent provides an orange solid which was purified by flash chromatography (SiO2), yielding the title compound as an orange solid (81%). M.p.: 114°-116° C. 1H-NMR (300 MHz, [D] acetone): δ=8.24 (s, 1H), 7.63 (d, 1H, 3J=5.0 Hz), 7.52 (dd, 1H, 3J=3.7 Hz and 4J=0.7 Hz), 7.48 (s, 2H), 7.14 (dd, 1H, 3J=5.0 Hz and 3.7 Hz), 4.32 (q, 2H, 3J=7.2 Hz), 4.19 (q, 2H, 3J=7.1 Hz), 1.37 (t, 3H, 3J=7.1 Hz), 1.26 (t, 3H, 3J=7.1 Hz). 13C-NMR (300 MHz, [D] acetone): δ=165.0, 164.3, 161.1, 161.0, 146.1, 143.2, 132.8, 132.1, 130.5, 128.4, 101.8, 61.0, 60.0, 14.3, 14.1.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 20 hours
  2. customComplete removal of the solvent
  3. customprovides an orange solid which
  4. customwas purified by flash chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-3e57f0fec68446d89f8904372be54a71
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08034895B2

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