Methyl iodide → N-(4-Bromophenyl)-N-methyl-formamide

HRID 2389588Notes

Reaction equation

HRID 2389588 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:14]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:14])[CH:9]=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 17474Formamide, N-(4-bromophenyl)-HCID 24758Sodium hydride

Product 1

HCID 15004464N-(4-Bromophenyl)-N-methyl-formamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-(4-bromophenyl)-formamide 50 (250 mg, 1.25 mmol) in DMF (3 mL) is added dropwise to a suspension of sodium hydride (65 mg, 1.63 mmol, 60% dispersion in mineral oil) in DMF (3 mL) at 0° C. After stirring 1 h, iodomethane (113 μl, 1.63 mmol) is added, the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with water (10 mL) and extracted into EtOAc (3×10 mL). The combined organic phases are dried over Na2SO4 and reduced in vacuo to give the title compound.

Workup

  1. stirringstirred 16 h
  2. customThe reaction is then quenched with water (10 mL)
  3. extractionextracted into EtOAc (3×10 mL)
  4. dry with materialThe combined organic phases are dried over Na2SO4

Sources & evidence

ORD record
ord-bd99bf4feda742e4a693a6a44924df6c
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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