Methyl iodide → HCID 71253145, compound

HRID 1029024Notes

Reaction equation

HRID 1029024 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:7].I[CH3:20]>C1COCC1>[Br:3][C:4]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]([N:8]([CH3:20])[CH2:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71253456HCID 71253456, compound

Product 1

HCID 71253145HCID 71253145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of NaH (60% in mineral oil) (0.122 mL, 2.81 mmol) in THF (5 ml) was added dropwise a solution of 2-bromo-3-methyl-N-neopentylbenzamide (400 mg, 1.407 mmol) in THF (1 ml) at RT. After 20 min, iodomethane (0.096 mL, 1.548 mmol) was added and the reaction was allowed to stir for 48 h. The reaction was quenched by the addition of water and EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (6-48% EtOAc/hexanes). 2-Bromo-N,3-dimethyl-N-neopentylbenzamide was isolated as a clear colorless viscous oil.

Workup

  1. customThe reaction was quenched by the addition of water and EtOAc
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash chromatography (6-48% EtOAc/hexanes)

Sources & evidence

ORD record
ord-233319aa78e743faaad9d1cc6fd97ccb
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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