Phenacyl bromide → 3,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-4-phenacyl-2H-1,4-benzoxazine

HRID 37123ノート

反応式

HRID 37123 の反応式
[CH3:1][C:2]1([CH3:16])[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1.[H-].[Na+].[CH2:19](Br)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>CN(C)C=O>[CH3:1][C:2]1([CH3:16])[C:7](=[O:8])[N:6]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1

参加物

5

反応物 3

HCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 106566312,2-Dimethyl-6-nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

生成物 1

HCID 107358923,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-4-phenacyl-2H-1,4-benzoxazine収率 66.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In an argon gas stream, 2.0 g of 3,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-2H-1,4-benzoxazine was added gradually to 0.4 g of 60% sodium hydride in oil in 40 ml of dry N,N-dimethylformamide. The mixture was stirred at room temperature for 1 hour and 2.68 g of phenacyl bromide was added. The mixture was stirred at room temperature for 1 hour, after which the solvent was distilled off under reduced pressure. The residue was diluted with 50 ml of water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column and elution was carried out with methylene chloride-ethyl acetate. Recrystallization from ethyl acetate-ether gave 2.04 g of 3,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-4-phenacyl-2H-1,4-benzoxazine.

後処理

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. distillationafter which the solvent was distilled off under reduced pressure
  3. additionThe residue was diluted with 50 ml of water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column and elution
  8. customRecrystallization from ethyl acetate-ether

出典と根拠

ORDレコード
ord-501f70b46e3f4601b7c88282c61ae676
出典データセット
uspto-grants-1995_05
特許番号
US05420126

反応ノート

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