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

HRID 25145

반응식

HRID 25145 반응식
[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]

참가 물질

4

반응물 2

HCID 887Methanol2회HCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-67d4f4c14c9d4d6ca9700aa849fccfb8
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858621B2

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