Potassium Iodide → HCID 22291412, compound

HRID 967831Notes

Reaction equation

HRID 967831 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]=[C:15]2[C:25]([F:28])([F:27])[F:26])=[CH:10][CH:9]=1)(=O)=O.[N-:29]=[N+:30]=[N-:31].[Na+].[I-].[K+]>CN(C=O)C>[N:29]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]=[C:15]2[C:25]([F:28])([F:27])[F:26])=[CH:10][CH:9]=1)=[N+:30]=[N-:31]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 33557Sodium AzideHCID 22291385HCID 22291385, compound

Product 1

HCID 22291412HCID 22291412, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-{4-[4-phenyl-2-(trifluoromethyl)-1H-imidazol-1-yl]phenyl}ethyl methanesulfonate and sodium azide (175 mg, 2.70 mmol) and potassium iodide (224 mg, 1.35 mmol) in DMF (7 mL) was heated at 100° C. for overnight. After cooling, the reaction mixture was partitioned between ethyl acetate (20 mL) and water (10 mL). The aqueous phase was extracted with ethyl acetate (3×10 mL) and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 10:1 to 4:1) to afford 450 mg (93%) of the title compound as colorless amorphous: MS (EI) m/z 357 [M]+.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate (20 mL) and water (10 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×10 mL)
  4. dry with materialthe combined organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 10:1 to 4:1)

Sources & evidence

ORD record
ord-e9f212cdb30743359013368e19bfa04b
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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