Methyl iodide → 3-bromo-4-chloro-N-(2-methoxy-phenyl)-N-methyl-benzamide

HRID 448857Notes

Reaction equation

HRID 448857 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])=[O:6].[H-].[Na+].I[CH3:23]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])[CH3:23])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 686027883-bromo-4-chloro-N-(2-methoxy-phenyl)-benzamide

Product 1

HCID 686027713-bromo-4-chloro-N-(2-methoxy-phenyl)-N-methyl-benzamideYield 78.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-bromo-4-chloro-N-(2-methoxy-phenyl)-benzamide (13.5 g, 39 mmol) in DMF (100 mL) at 0-5° C., was added NaH (1.9 g, 46.8 mmol, 60% in mineral oil) in several portions, followed by addition of iodomethane (3.15 mL, 50.7 mmol). The mixture was stirred at room temperature for 4 hrs and was partitioned between ethyl acetate and water. The organic layer was then washed with 1N HCl, saturated NaHCO3, brine and dried over MgSO4. Filtration over a silica gel pad followed by concentration and crystallization from ether/hexane yielded 3-bromo-4-chloro-N-(2-methoxy-phenyl)-N-methyl-benzamide (10.9 g) as a white solid. MS (M+H)+: 353.9, tR=2.812 min (method 1); NMR (CDCl3), 6, 7.62 (1H, d, J=1.5 Hz), 7.23-7.09 (3H, m), 7.06-7.00 (1H, m), 6.88-6.78 (2H, m), 3.75 (3H, s), 3.34 (3H, s)

Workup

  1. customwas partitioned between ethyl acetate and water
  2. washThe organic layer was then washed with 1N HCl, saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration over a silica gel pad
  5. concentrationfollowed by concentration and crystallization from ether/hexane

Sources & evidence

ORD record
ord-0241ba13cb9a43228857424b8e51af54
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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