Sodium Carbonate → HCID 22387856, compound

HRID 1976777Notes

Reaction equation

HRID 1976777 reaction equation
[Br-].O=[C:3]([CH3:16])[CH2:4][N+:5]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:7][C:6]=1[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:16][C:3]1[CH:15]=[C:6]2[N:5]([CH:4]=1)[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 21998742HCID 21998742, compound

Product 1

HCID 22387856HCID 22387856, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 50A (570 mg, 2.32 mmol) and sodium carbonate (400 mg, 5.0 mmol) in ethanol (10 mL) was refluxed for 3 hours and concentrated. The concentrate was dissolved in dichloromethane, and this solution was washed with water, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/dichloromethane to provide 407 mg (93%) of the desired product.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in dichloromethane
  3. washthis solution was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/dichloromethane

Sources & evidence

ORD record
ord-fb9245b1b01946eaac7b9da2faf7b7ea
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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