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

HRID 2386761ノート

反応式

HRID 2386761 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9a6bb6a16b1546f2ab15f3e2ca2e364a
出典データセット
uspto-grants-2012_09
特許番号
US08268820B2

反応ノート

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