Water → HCID 21472090, compound

HRID 2294873Notes

Reaction equation

HRID 2294873 reaction equation
[N:1]1[C:2](=[O:13])[CH2:3][C:4](=[O:12])[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:21]([CH3:23])[CH3:22].O>CS(C)=O.C(OCC)(=O)C>[CH3:22][CH:21]([N:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:12])[CH2:3][C:2]1=[O:13])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 21472088HCID 21472088, compound

Product 1

HCID 21472090HCID 21472090, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1,5-benzodiazepine-2,4-dione (5.5 g, 0.031 mole) in DMSO (70 mL) was treated with cesium carbonate (10.17 g, 0.031 mole) and 2-iodopropane (5.27 g, 0.03 1 mole). The reaction was heated to 80° C. for two hours and then stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate (400 mL) and poured into water (500 mL). The organic layer was separated and the aqueous layer was extracted again with ethyl acetate (400 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 3:1 ethyl acetate:hexane to give 560 mg of product.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted again with ethyl acetate (400 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 3:1 ethyl acetate

Sources & evidence

ORD record
ord-50b7b5feb380420e974fb819b3f684da
Source dataset
uspto-grants-1997_11
Patent number
US05691331

Reaction notes

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