Dimethylformamide → HCID 23086889, compound

HRID 2186725Notes

Reaction equation

HRID 2186725 reaction equation
OCC[CH:4]1[CH2:9][NH:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:13]([OH:14])[C:6]=2[O:5]1.[C:15](=[O:18])([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].[CH3:27]N(C=O)C>>[OH:18][CH2:15][CH2:27][N:8]1[C:7]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:6]=2[O:5][CH2:4][CH2:9]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 86758189HCID 86758189, compound

Product 1

HCID 23086889HCID 23086889, compoundYield 60%

Procedure

4-(2-(hydroxyethyl)-8-hydroxy-3,4-dihydro-2H-1,4-benzoxazine (4.66 g) was dissolved in anhydrous DMF (50 ml), and anhydrous potassium carbonate (8.50 g) and methyl bromoacetate (4.0 ml) were added to the resultant solution, and the mixture was stirred at room temperature for 6 hours. The solvent was distilled off, and the residue was poured into 5% citric acid, and then extracted with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over magnesium sulfate, and then concentrated. The residue was recrystallized from ethyl acetate/n-hexane to obtain the object compound (3.83 g, yield 60%).

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was poured into 5% citric acid
  3. extractionextracted with ethyl acetate
  4. washThe resultant organic layer was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-4b6bcb33209d49cb95529472603a3dc2
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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