Iodoethane → 2H-1,4-Benzoxazin-3(4H)-one, 4-ethyl-

HRID 2096778노트

반응식

HRID 2096778 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.[H-].[Na+].[CH2:14](I)[CH3:15]>CN(C)C=O>[CH2:14]([N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][C:3]1=[O:11])[CH3:15]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 727572H-1,4-benzoxazin-3(4H)-one

생성물 1

HCID 138630252H-1,4-Benzoxazin-3(4H)-one, 4-ethyl-수율 93.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a cooled solution of 2H-1,4-benzoxazin-3(4H)-one (11.93 g, 80 mmol) in N,N-dimethylformamide (120 ml) was added sodium hydride (60% dispersion in mineral oil, 3.2 g, 80 mmol) in portions between 0° C. and 5° C. (1 h). The mixture was stirred 1 h at 0° C. To the cooled mixture was added ethyl iodide (13.7 g, 88 mmol) dropwise. The ice bath was removed and the mixture was stirred at r.t. for 17 h. The mixture was poured on water and extracted twice with AcOEt. The organic layers were washed with brine and water, dried (MgSO4) and concentrated. The crude product was purified by column chromatography (silica gel, heptane/AcOEt 9:1) to give the title compound (13.3 g) as colorless oil.

후처리

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at r.t. for 17 h
  3. additionThe mixture was poured on water
  4. extractionextracted twice with AcOEt
  5. washThe organic layers were washed with brine and water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel, heptane/AcOEt 9:1)

출처 및 근거

ORD 기록
ord-d6d5111f8fa94133b3512028f9724436
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450313B2

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