Methyl iodide → 8-Chloro-1-methyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

HRID 544989Notes

Reaction equation

HRID 544989 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][C:8](=[O:13])[NH:7][C:6]=2[CH:14]=1.[C:15](=O)([O-])[O-].[Cs+].[Cs+].CI>C1COCC1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][C:8](=[O:13])[N:7]([CH3:15])[C:6]=2[CH:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11390173HCID 11390173, compound

Product 1

HCID 669346558-Chloro-1-methyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dioneYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

8-Chloro-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (iv-j) (0.2 g, 1 mmol) was dissolved in a mixture of THF (10 mL) and DMF (2 mL). Cesium carbonate (0.98 g, 3 mmol) and methyl iodide (0.069 mL, 1.1 mmol) were added and the reaction mixture was stirred at room temperature for 3 h. The mixture was concentrated under reduced pressure and dichloromethane (10 mL) was added. The inorganic precipitate was filtered and the filtrate was concentrated under reduced pressure to give a viscous residue. This residue was purified utilizing column chromatography, eluting with 50% ethyl acetate/hexane to afford the title compound as a white solid (0.1 g, 45%): MS m/z=224 (M+H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and dichloromethane (10 mL)
  2. additionwas added
  3. filtrationThe inorganic precipitate was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give a viscous residue
  6. customThis residue was purified utilizing column chromatography
  7. washeluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9fb759a6fc80495ebcce273eaff169de
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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