Thioacetamide → HCID 10062363, compound

HRID 855903Notes

Reaction equation

HRID 855903 reaction equation
Br[CH:2]1[C:8](=O)[C:7]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:6]=2[O:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.[C:19]([NH2:22])(=[S:21])[CH3:20]>CN(C)C=O>[F:14][C:11]1[CH:12]=[CH:13][C:6]2[O:5][C:4]3[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=3[C:2]3[S:21][C:19]([CH3:20])=[N:22][C:8]=3[C:7]=2[CH:10]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 69515148HCID 69515148, compound

Product 1

HCID 10062363HCID 10062363, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 11-bromo-8-fluoro-11H-dibenzo[b,f]oxepin-10-one (2.34 mmoles) in dry N,N-dimethylformamide (12 ml), thioacetamide (2.8 mmoles) was added. The reaction mixture was heated under stirring at 90° C. for 3 hours. Then the solvent was evaporated under reduced pressure and the remaining oily product was dissolved in ethyl acetate and water. After extraction the organic layers were washed with a saturated aqueous NaHCO3 solution, water and a saturated aqueous sodium chloride solution. After purification by chromatography on a silica gel column, a crystalline product was isolated.

Workup

  1. temperatureThe reaction mixture was heated
  2. customThen the solvent was evaporated under reduced pressure
  3. dissolutionthe remaining oily product was dissolved in ethyl acetate
  4. extractionAfter extraction the organic layers
  5. washwere washed with a saturated aqueous NaHCO3 solution, water
  6. customAfter purification by chromatography on a silica gel column
  7. customa crystalline product was isolated

Sources & evidence

ORD record
ord-057d2d01998242818ae1eebc985b721e
Source dataset
uspto-grants-2007_08
Patent number
US07262302B2

Reaction notes

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