Dimethylformamide → 4-iodo-N,N,3-trimethylaniline

HRID 340389Notes

Reaction equation

HRID 340389 reaction equation
[I:1][C:2]1[CH:8]=[CH:7]C(N)=[CH:4][C:3]=1[CH3:9].C([O-])(O)=O.[Na+].IC.[CH3:17][N:18]([CH:20]=O)[CH3:19]>C(OCC)(=O)C.O>[I:1][C:2]1[CH:8]=[CH:7][C:20]([N:18]([CH3:19])[CH3:17])=[CH:4][C:3]=1[CH3:9]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 27342754-Iodo-3-methylaniline

Product 1

HCID 668749314-iodo-N,N,3-trimethylaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-iodo-3-methylaniline (commercially available) (1 eq), NaHCO3 (2.5 eq), and iodomethane (2.5 eq), in DMF ((0.2M) was stirred at ambient temperature overnight. The reaction mixture was then diluted with ethyl acetate and water. The two phases were separated, and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane and 4-iodo-N,N,3-trimethylaniline was isolated as a yellow solid.

Workup

  1. customThe two phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated en vacuo
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  7. customwas isolated as a yellow solid

Sources & evidence

ORD record
ord-5bf949934bd841a3b55d5656a99b9565
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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