Methyl iodide → HCID 58265699, compound

HRID 1874079Notes

Reaction equation

HRID 1874079 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([Cl:12])[CH:6]=1)=[O:3].[H-].[Na+].[CH3:15]I>C1COCC1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]([CH3:15])[C:2](=[O:3])[CH3:1])=[CH:6][C:7]=1[Cl:12]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 2746295N-(4-Bromo-3-chlorophenyl)acetamide

Product 1

HCID 58265699HCID 58265699, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-3-chloroacetanilide (10.0 g, 40.2 mmol) in 50 mL THF is added 60% sodium hydride in mineral oil (2.40 g, 60.0 mmol) and the reaction mixture is stirred for 1 h at RT. The reaction mixture is cooled to 0° C., methyliodide (2.49 mL, 40.0 mmol) is added. After 2 h additional methyl iodide (0.25 mL, 4.0 mmol) is added and the reaction mixture is stirred at RT for 10 min. The reaction mixture is quenched with saturated aqueous ammonium chloride, filtered and extracted with diethyl ether. The organic phases are washed with brine, dried over Na2SO4 and evaporated to dryness. Yield: 10.3 g.

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. stirringthe reaction mixture is stirred at RT for 10 min
  3. customThe reaction mixture is quenched with saturated aqueous ammonium chloride
  4. filtrationfiltered
  5. extractionextracted with diethyl ether
  6. washThe organic phases are washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-81812a8da37240fcbe1a04f9cf70e2a2
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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