Cesium carbonate → HCID 21472092, compound

HRID 2294874Notes

Reaction equation

HRID 2294874 reaction equation
[CH3:1][CH:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=[O:15])[CH2:6][C:5]1=[O:16])[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].[F:23][C:24]([F:28])([F:27])[CH2:25]I.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:3][CH:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:25][C:24]([F:28])([F:27])[F:23])[C:7](=[O:15])[CH2:6][C:5]1=[O:16])[CH3:1]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 516892Sodium BicarbonateHCID 21472090HCID 21472090, compound

Product 1

HCID 21472092HCID 21472092, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1-(2-propyl)-1,5-benzodiazepine-2,4-dione (0.55 g, 0.0025 mole) in N,N-dimethylformamide (5 mL) at room temperature was treated with cesium carbonate (1.64 g, 0.005 mole) and trifluoroethyl iodide (1.06g, 0.005 mole), and heated to 80° C. for 2 hours. The reaction was cooled to room temperature and poured into a solution of saturated sodium hydrogen carbonate (100 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 1:1 ethyl acetate/hexane to give 440 mg of product.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-a0588ce7d3154624baa725d76ea45711
Source dataset
uspto-grants-1997_11
Patent number
US05691331

Reaction notes

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