Methyl iodide → 2,2,2-trifluoro-N-(4-iodophenyl)-N-methylacetamide

HRID 1944865Notes

Reaction equation

HRID 1944865 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)=[O:4].CI.[C:17]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[F:14][C:2]([F:1])([F:13])[C:3]([N:5]([C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)[CH3:17])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6869622,2,2-trifluoro-N-(4-iodophenyl)acetamide

Product 1

HCID 210712382,2,2-trifluoro-N-(4-iodophenyl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

Intermediate 32 (1.0 g, 3.175 mmol) in 20 mL of acetone was combined with CH3I (6.350 mmol, 0.901 g, 0.395 mL) and K2CO3 (6.350 mmol, 0.876 g) then refluxed at 80° C. for 2 hours. The reaction was worked up quenching the reaction with 1× saturated NaHCO3, extracted 4×25 mL EtOAc then washed 1× water, 1× saturated NaCl, dried over Na2SO4, then concentrated. The product was carried through without purification. ES/MS calcd. for C9H7F3INO 328.95. Found m/z=330 (M+H)+.

Workup

  1. customThe reaction was worked up quenching
  2. customthe reaction with 1× saturated NaHCO3
  3. extractionextracted 4×25 mL EtOAc
  4. washthen washed 1× water, 1× saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe product was carried through without purification

Sources & evidence

ORD record
ord-2cef5db262504f71ae008f9fb94b1e4a
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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