Methyl iodide → N-(4-bromophenyl)-N-methylacetamide

HRID 2389594

Reaction equation

HRID 2389594 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:3].[H-].[Na+].I[CH3:15]>CN(C=O)C>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]([CH3:15])[C:2](=[O:3])[CH3:1])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 76834'-BromoacetanilideHCID 24758Sodium hydride

Product 1

HCID 4324567N-(4-bromophenyl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

4-bromoacetanilide (1.0 g, 4.67 mmol) in DMF (5 mL) is added dropwise to a suspension of sodium hydride (224 mg, 5.61 mmol, 60% dispersion in mineral oil) in DMF (5 mL) at 0° C. After stirring 1 h at 0° C., iodomethane (349 μl, 5.61 mmol) is added and the reaction mixture warmed to RT and stirred 16 h. The reaction is quenched with water (15 mL) and extracted into EtOAc (3×15 mL); the combined organic phases are then dried over Na2SO4 and reduced in vacuo. Purification by column chromatography (40% EtOAc in heptane) gives the title compound.

Workup

  1. temperaturethe reaction mixture warmed to RT
  2. stirringstirred 16 h
  3. customThe reaction is quenched with water (15 mL)
  4. extractionextracted into EtOAc (3×15 mL)
  5. dry with materialthe combined organic phases are then dried over Na2SO4
  6. customPurification by column chromatography (40% EtOAc in heptane)

Sources & evidence

ORD record
ord-738712915e8d4a81afff40dacc58d9e6
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Linked notes

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