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

HRID 2422516노트

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HRID 2422516 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bde0578f06204f3ea4e1fc509bb4d86f
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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