Dimethylformamide → HCID 10490884, compound

HRID 1635042Notes

Reaction equation

HRID 1635042 reaction equation
O1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][C:3](=[O:11])[NH:2]1.[C:12](=[O:15])([O-])[O-].[K+].[K+].C[N:19]([CH:21]=O)C>O>[C:21]([C:7]1[CH:6]=[C:5]([CH:4]2[C:3](=[O:11])[NH:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:12]=3[O:15]2)[CH:10]=[CH:9][CH:8]=1)#[N:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 199374482H-1,2-Benzoxazin-3(4H)-one

Product 1

HCID 10490884HCID 10490884, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the benzoxazinone (I6) (1.38 g, 4.17 mmol) in DMF (5 mL) was added potassium carbonate (1.40 g, 10.1 mmol), and the solution was stirred at room temperature for 1 hour. The solution was diluted with water and extracted with ethyl acetate (3×150 mL). The combined organic extracts were washed with brine (2×100 mL), dried with magnesium sulfate filtered, and evaporated in vacuo. The residue was purified on a silica gel column eluted with 25% ethyl acetate in dichloromethane. The product (I1) was isolated 0.48 g (46%) as a light orange solid.

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe combined organic extracts were washed with brine (2×100 mL)
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified on a silica gel column
  7. washeluted with 25% ethyl acetate in dichloromethane
  8. customThe product (I1) was isolated 0.48 g (46%) as a light orange solid

Sources & evidence

ORD record
ord-554a3ee4d6544b24b4d89cd8fe608e5d
Source dataset
uspto-grants-2003_01
Patent number
US06509335B1

Reaction notes

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