Lawesson's reagent → 2-Ethyl-8-methyl-1-thia-4,8-diaza-spiro[4.5]decane-3-thione

HRID 1825850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825850
[CH3:1][CH2:2][CH:3]1[S:8][C:7]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[NH:6][C:4]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C(#N)C>[CH2:2]([CH:3]1[C:4](=[S:24])[NH:6][C:7]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[S:8]1)[CH3:1]

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 11528611HCID 11528611, Verbindung

Produkt 1

HCID 104664182-Ethyl-8-methyl-1-thia-4,8-diaza-spiro[4.5]decane-3-thione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of AF267 (214 mg, 1 mmol) and Lawesson's Reagent (280 mg, 0.692 mmol) in acetonitrile (5 ml) was heated under reflux for 17 hrs. The solvent was removed and residue was dissolved in concentrate aqueous sodium carbonate (0.5 ml) and then extracted with ethyl acetate. The extract was dried and the solvent evaporated. The residue (250 mg), recrystallized first from toluene and then from acetonitrile gave pure AF510. 1H-NMR (CDCl3) δ 1.03 (t, CH3CH2), 1.83 (m), 1.93–2.44 (m), 2.30 (s, CH3N), 2.80 (m, 2H), 4.21 (dd, SCH), 8.66 (br, NH) ppm. MS m/e 230 (M30), 197 (M+−SH), 156, 128, 96 (100%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hrs
  3. customThe solvent was removed
  4. dissolutionresidue was dissolved in concentrate aqueous sodium carbonate (0.5 ml)
  5. extractionextracted with ethyl acetate
  6. customThe extract was dried
  7. customthe solvent evaporated
  8. customThe residue (250 mg), recrystallized first from toluene
  9. customfrom acetonitrile gave pure AF510

Quellen und Nachweise

ORD-Eintrag
ord-d649a37378234ea183ec6d76a17e7d3d
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049321B2

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