N-Iodosuccinimide → HCID 178506276, compound

HRID 1488092Notes

Reaction equation

HRID 1488092 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([I:26])C(=O)C1>CC#N.O>[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([I:26])=[C:13]([C:15]([F:17])([F:18])[F:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178506256HCID 178506256, compound2×

Product 1

HCID 178506276HCID 178506276, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 2-((benzyloxy)methyl)-4-(trifluoromethyl)-1H-imidazole (compound 219.1, 1.5 g, 5.85 mmol) in CH3CN (18 mL). NIS (1.6 g, 7.02 mmol) was added to the reaction. The reaction mixture was stirred for 15 h at 85. The reaction mixture was diluted with 30 mL of H2O. The aqueous phase was extracted with 2×30 mL of ethyl acetate. The combined organic layers were washed with 2×20 mL of Na2S2O3(sat.) and 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:100-1:2) as eluent to furnish 0.7 g (31%) of the title compound as a yellow oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionThe aqueous phase was extracted with 2×30 mL of ethyl acetate
  3. washThe combined organic layers were washed with 2×20 mL of Na2S2O3(sat.) and 2×20 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:100-1:2) as eluent

Sources & evidence

ORD record
ord-d74f81f65b33481f870a121ddd753b98
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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