Trifluoroacetic acid → HCID 58497204, compound

HRID 1254066Notes

Reaction equation

HRID 1254066 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[N:4]=[CH:3]1.C(O)(C(F)(F)F)=O.C1C(=O)N([I:31])C(=O)C1>C(Cl)Cl>[I:31][C:6]1[N:2]([CH3:1])[CH:3]=[N:4][C:5]=1[C:7]1[CH:8]=[CH:9][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 58497227HCID 58497227, compound

Product 1

HCID 58497204HCID 58497204, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 1-methyl-4-[4-(methylsulfonyl)phenyl]-1H-imidazole (2.3 g, 9.73 mmol) in CH2Cl2 (6 ml) was added TFA (3.0 ml, 38.9 mmol), and NIS (2.41 g, 10.71) at rt. After being stirred at rt for 3 h, the reaction mixture was diluted with CH2Cl2, quenched with NaHCO3 (aq), washed with aq Na2S2O3, water and brine. Dried over Na2SO4, filtered and concentrated to afford 5-iodo-1-methyl-4-[4-(methylsulfonyl)phenyl]-1H-imidazole (3.4 g) which was used in the next step without further purification. LCMS: [M+1]+=363.0

Workup

  1. customquenched with NaHCO3 (aq)
  2. washwashed with aq Na2S2O3, water and brine
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6864068c68346b485cab0f4b165edf8
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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