Iodine → HCID 13981859, compound

HRID 1866157Notes

Reaction equation

HRID 1866157 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][C@H:6]([CH3:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].S(=O)(=O)(O)O.II.O.O.[I:26](O)(=O)(=O)=O>C(O)(=O)C.O>[F:1][C:2]([F:15])([F:16])[C:3]([NH:5][C@H:6]([CH3:14])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([I:26])=[CH:10][CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 148772362,2,2-Trifluoro-N-[(2R)-1-phenylpropan-2-yl]acetamideHCID 86590690HCID 86590690, compound

Product 1

HCID 13981859HCID 13981859, compoundYield 185.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,2,2-trifluoro-N-[(1R)-1-methyl-2-phenylethyl]acetamide (3.75 g) in acetic acid (32 ml)—water (6.5 ml)—sulfuric acid (0.97 ml) were added iodine (1.65 g) and periodic acid dihydrate (740 mg) at room temperature, and the mixture was heated to 60-80° C. for 5 hours. After being allowed to cool to room temperature, the mixture was partitioned between hexane/ethyl acetate and water. The organic layer was separated, washed successively with water, sodium sulfite solution, water and brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was recrystallized from diisopropyl ether (44 ml) to give 2,2,2-trifluoro-N-[(1R)-2-(4-iodophenyl)-1-methylethyl]acetamide (2.15 g) as a colorless needle.

Workup

  1. temperatureto cool to room temperature
  2. customthe mixture was partitioned between hexane/ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed successively with water, sodium sulfite solution, water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was recrystallized from diisopropyl ether (44 ml)

Sources & evidence

ORD record
ord-e6524968bccc4ad7869092a7003e6b7b
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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