Acetamide → 7-methyl-4-(2-methyl-1,3-oxazol-4-yl)-2H-chromen-2-one

HRID 2422516Notes

Reaction equation

HRID 2422516 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([CH3:15])=[CH:12][CH:13]=2)[O:8][C:7](=[O:16])[CH:6]=1)=O.[C:17]([NH2:20])(=[O:19])[CH3:18].C(OCC)(=O)C>CN(C)C=O>[CH3:15][C:11]1[CH:10]=[C:9]2[C:14]([C:5]([C:3]3[N:20]=[C:17]([CH3:18])[O:19][CH:2]=3)=[CH:6][C:7](=[O:16])[O:8]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 8857Ethyl AcetateHCID 866219744-(bromoacetyl)-7-methyl-2H-chromen-2-one

Product 1

HCID 866219757-methyl-4-(2-methyl-1,3-oxazol-4-yl)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(bromoacetyl)-7-methyl-2H-chromen-2-one (750 mg, 2.67 mmol) in N,N-dimethylformamide (2.5 mL), acetamide (158 mg, 2.67 mmol) was added. The reaction was then stirred overnight at 100° C. After cooling, the reaction mixture was dissolved with ethyl acetate and washed with water and brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was pre-adsorbed on silica gel and purified by column chromatography (EtOAc/hexanes, 30:70 to 80:20) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.52 (s, 1H), 8.21 (d, 1H), 7.23 (s, 1H), 7.21 (d, 1H), 6.52 (s, 1H), 2.57 (s, 3H), 2.49 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. custompurified by column chromatography (EtOAc/hexanes, 30:70 to 80:20)

Sources & evidence

ORD record
ord-bde0578f06204f3ea4e1fc509bb4d86f
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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