Sodium hydride → (5-Nitro-3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methanol

HRID 896008노트

반응식

HRID 896008 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH:12]2[CH2:14][O:13]2)[C:5]=1[NH2:15])([O-:3])=[O:2].[H-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[C:5]2[NH:15][CH:12]([CH2:14][OH:13])[CH2:11][O:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 113448381-(2-Amino-3-nitrophenoxy)-2,3-epoxypropane

생성물 1

HCID 22349487(5-Nitro-3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methanol수율 74.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-nitro-6-oxiranylmethoxy-phenylamine (14.7 g, 0.070 mol) in DMF (200 mL) was added sodium hydride (3.5 g, 60 wt. %, 0.087 mol). The resulting reaction mixture was stirred at room temperature overnight. The mixture was evaporated in vacuum, the residue diluted with water (200 mL) and extracted with methylene chloride (2×200 mL). The combined organic layers were washed with water (300 mL) and saturated sodium chloride solution (300 mL), dried (Na2SO4) and concentrated to provide the title compound as a dark red crystal (11.0 g). 1H NMR (DMSO-d6): δ 8.30 (d, 1H); 7.60 (dd, 1H); 7.00 (dd, 1H); 6.65 (dd, 1H); 5.15 (t, 1H); 4.10 (m, 2H); 3.70 (m, 1H); 3.50 (m, 2H).

후처리

  1. customThe resulting reaction mixture
  2. customThe mixture was evaporated in vacuum
  3. additionthe residue diluted with water (200 mL)
  4. extractionextracted with methylene chloride (2×200 mL)
  5. washThe combined organic layers were washed with water (300 mL) and saturated sodium chloride solution (300 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-35f1276ba2874e849f0808c0c0954568
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919334B2

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