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

HRID 324466Notes

Reaction equation

HRID 324466 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-34fcf72cec264a9986a2cffd6fb24021
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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