Sodium Iodide → HCID 14763125、化合物

HRID 275130

反応式

HRID 275130 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:27][O:26][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:16]=1[CH2:15][N:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:12][CH2:11][CH2:10]1)[C:20]([O:22][CH3:23])=[O:21]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazine

生成物 1

HCID 14763125HCID 14763125、化合物収率 84%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 6-nitro-2,3-dihydrobenz-1,4-oxazine (0.45 g.), methyl 4-bromomethyl-3-methoxybenzoate (B) (0.65 g.), anhydrous potassium carbonate (0.35 g.), sodium iodide (0.38 g.) and acetone (25 ml.) was stirred and heated under reflux for 48 hours, under an atmosphere of nitrogen. The cooled reaction mixture was separated by filtration. The residue was washed with acetone, and the filtrate and washings were evaporated. The resulting solid was dissolved in dichloromethane and residual solid removed by filtration. The filtrate was evaporated. The product was purified by flash chromatography on silica gel (3 cm. diameter column), eluting with 1:10 v/v ethyl acetate: toluene, to give methyl 3-methoxy-4-(6-nitro-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate (G) (0.75 g., 84%), m.p. 130°-132° C.; NMR (80 MHz, CDCl3): 3.0(t,2H, OCH2.CH2N), 3.8(s,3H, OCH3), 3.95(s,3H, OCH3), 4.3(t, 2H, OCH2.CH2N), 4.5(s,2H, CH2.Ar), 6.8(d,1H), 7.5(m, 5H).

後処理

  1. temperatureheated
  2. temperatureunder reflux for 48 hours, under an atmosphere of nitrogen
  3. customThe cooled reaction mixture
  4. customwas separated by filtration
  5. washThe residue was washed with acetone
  6. customthe filtrate and washings were evaporated
  7. dissolutionThe resulting solid was dissolved in dichloromethane
  8. customresidual solid removed by filtration
  9. customThe filtrate was evaporated
  10. customThe product was purified by flash chromatography on silica gel (3 cm. diameter column)
  11. washeluting with 1:10 v/v ethyl acetate

出典と根拠

ORDレコード
ord-62eea3f9fbb947429f40dbed005140ca
出典データセット
uspto-grants-1995_02
特許番号
US05391758

関連ノート

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