N-Iodosuccinimide → HCID 178432833, compound

HRID 1488091Notes

Reaction equation

HRID 1488091 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.C1C(=O)N([I:18])C(=O)C1>CC#N.O>[I:18][C:4]1[NH:3][C:2]([CH3:1])=[N:6][C:5]=1[C:7]([F:10])([F:9])[F:8]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178432834HCID 178432834, compound2×

Product 1

HCID 178432833HCID 178432833, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 2-methyl-4-(trifluoromethyl)-1H-imidazole (compound 16.2, 1.72 g, 11.46 mmol) in CH3CN (25 mL). NIS (3.87 g, 17.20 mmol) was added to the reaction. The reaction mixture was stirred overnight at 85. The reaction mixture diluted with 50 mL of H2O and extracted with 3×30 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. This resulted in 4.32 g (crude) of the title compound as a brown oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionextracted with 3×30 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

Sources & evidence

ORD record
ord-095f6a4879a741afaa329ab33dbb6185
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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