Thioacetamide → 7-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

HRID 2116665

Reaktionsgleichung

Reaktionsgleichung von HRID 2116665
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13](=O)[CH2:14]Br)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[C:17]([NH2:20])(=[S:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[N:20]=[C:17]([CH3:18])[S:19][CH:14]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 2723949ThioacetamideHCID 233702397-bromo-4-(bromoacetyl)-2H-chromen-2-one

Produkt 1

HCID 598148377-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 7-bromo-4-(bromoacetyl)-2H-chromen-2-one (0.605 g, 1.7 mmol) in DMF was added thioacetamide (0.138 g, 1.8 mmol). The mixture was stirred 24 h at rt and at 100° C. overnight. Once cool to rt, it was partitioned between aqueous NH4Cl and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue swished in hexanes/Et2O to give the title compound.

Aufarbeitung

  1. temperatureOnce cool to rt
  2. customit was partitioned between aqueous NH4Cl and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c33af81955c0450cb8ae90c00e01350a
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439260B2

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