Triethylamine → 4,4,6,6-Tetramethyl-4,6-dihydrofuro[3,4-d]thiazol-2-amine

HRID 1028164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028164
Br[CH:2]1[C:6]([CH3:8])([CH3:7])[O:5][C:4]([CH3:10])([CH3:9])[C:3]1=O.[NH2:12][C:13]([NH2:15])=[S:14].C(N(CC)CC)C>C(O)C>[CH3:7][C:6]1([CH3:8])[C:2]2[N:12]=[C:13]([NH2:15])[S:14][C:3]=2[C:4]([CH3:10])([CH3:9])[O:5]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2723790ThioureaHCID 122017454-Bromo-2,2,5,5-tetramethyldihydrofuran-3(2h)-one

Produkt 1

HCID 790063024,4,6,6-Tetramethyl-4,6-dihydrofuro[3,4-d]thiazol-2-amineAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of Example 1A (10.0 g, 0.045 mol) in ethanol (100 mL) were added thiourea (3.8 g, 0.05 mol) and triethylamine (6.3 mL, 0.045 mol). The reaction mixture was refluxed overnight, cooled and concentrated under reduced pressure. The residue was diluted with water (25 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-5% methanol in dichloromethane) to afford 1.3 g (15%) of the title compound. MS (ESI+) m/z 199 (M+H)+

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with water (25 mL)
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (SiO2, 0-5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-da22be07e4d0421fb133aa357346b87d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735434B2

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