Methanol → 6-nitro-3,4-dihydro-2H-1,4-benzoxazine

HRID 25145

反応式

HRID 25145 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=O)[NH:9][C:8]=2[CH:14]=1)([O-:3])=[O:2].CO>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:14]=1)([O-:3])=[O:2]

参加物

4

反応物 2

HCID 887Methanol2 回HCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one

生成物 1

HCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 6-nitro-4-H-benzo[1,4]oxazin-3-one (7.84 g, 40.38 mmol) in tetrahydrofuran (100 mL) was added a solution of 2.0M borane-methyl sulfide complex in tetrahydrofuran (91 mL, 181 mmol). The mixture was heated to reflux for 4.5 hours then allowed to stir overnight at room temperature. Methanol was added slowly to react with unreacted borane-methyl sulfide complex, which resulted a violent evolution of gas. When this subsided, excess methanol was added and the solution heated to reflux. After 2 hours the solution was cooled, the solvent evaporated under vacuum, and the residue triturated with ethyl acetate/hexane. An orange solid was filtered off which was rinsed with hexane, to yield 6-nitro-3,4-dihydro-2H-benzo[1,4]oxazine as a solid product. More of the solid was recovered as a second crop from the filtrate.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4.5 hours
  3. customto react with unreacted borane-methyl sulfide complex, which
  4. customresulted a violent evolution of gas
  5. temperaturethe solution heated to reflux
  6. temperatureAfter 2 hours the solution was cooled
  7. customthe solvent evaporated under vacuum
  8. customthe residue triturated with ethyl acetate/hexane
  9. filtrationAn orange solid was filtered off which
  10. washwas rinsed with hexane

出典と根拠

ORDレコード
ord-67d4f4c14c9d4d6ca9700aa849fccfb8
出典データセット
uspto-grants-2005_02
特許番号
US06858621B2

関連ノート

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