Sodium Carbonate → 3-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-5-carbaldehyde

HRID 863077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863077
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[CH:15]=[CH:14][NH:13][C:12]1=[S:16].[C:17]([O-])(=[O:19])C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.C1C=CC=CC=1>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[CH:15]=[C:14]([CH:17]=[O:19])[NH:13][C:12]1=[S:16]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 196993691-(1,2,3,4-Tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thioneHCID 178418268HCID 178418268, Verbindung

Produkt 1

HCID 196994073-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-5-carbaldehydeAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22229412AcOH benzeneLösungsmittel

Versuchsvorschrift

A suspension of 4-(1R,2R,3S,4)-tetrahydroxybut-1-yl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (0.252 g, 0.72 mmol) and lead tetraacetate (0.851 g, 1.92 mmol) in 15 mL of 33% acetic acid/benzene was stirred until the mixture was homogenous and 30 minutes. The reaction mixture was poured into 125 mL of saturated sodium carbonate solution and the mixture was filtered. The organic layer was separated, dried over magnesium sulfate and concentrated. The residue was dissolved in 40 mL of THF and 2 mL of sulfurous acid (6% SO2). Evaporation of the solvent gave 3-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-5-carbaldehyde (0.15 g, 0.59 mmol), m.p. 206°-210° C.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 40 mL of THF
  6. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-184c4e1a94324ca683b5ae83f9e53757
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719280

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