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

HRID 896008

反応式

HRID 896008 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-35f1276ba2874e849f0808c0c0954568
出典データセット
uspto-grants-2005_07
特許番号
US06919334B2

関連ノート

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