N-Bromosuccinamide → 2-Methyl-7-n-propyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-one

HRID 324466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 324466
[CH3:1][C:2]1[S:3][C:4]2[CH2:11][CH2:10][C:9]3[CH:12]=[C:13]([CH2:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:8]=3[C:7](=[O:19])[C:5]=2[N:6]=1.BrNC(=O)CCC(N)=O>C(OCC)(=O)C>[CH3:1][C:2]1[S:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[C:13]([CH2:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:8]=3[C:7](=[O:19])[C:5]=2[N:6]=1

Komponenten

4

Edukt 2

HCID 9834204N-BromosuccinamideHCID 220036509,10-Dihydro-2-methyl-7-n-propyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-one

Produkt 1

HCID 220035872-Methyl-7-n-propyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product from step (ix) (2.8 g) and N-bromosuccinamide were dissolved in ethyl acetate (30 ml) and irradiated with a 500 Watt halogen lamp at reflux for 2 h. The solvent was evaporated under reduced pressure and the solid residue dissolved in dichloromethane (30 ml) and treated with triethylamine (10 ml). After 2 h the solvents were removed under reduced pressure and the residue partioned between water and ethyl acetate. The organic layer was collected and dried over MgSO4. The solvent was evaporated under reduced pressure and the product purified by flash chromatography.

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe solid residue dissolved in dichloromethane (30 ml)
  4. additiontreated with triethylamine (10 ml)
  5. customAfter 2 h the solvents were removed under reduced pressure
  6. customThe organic layer was collected
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated under reduced pressure
  9. customthe product purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-34fcf72cec264a9986a2cffd6fb24021
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218376B1

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