Sodium hydride → 8-(2,4-Dimethylphenyl)-2-methyl-4-(1-propylbutyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 598067ノート

反応式

HRID 598067 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[O:17][CH:16]([CH3:19])[C:15](=[O:20])[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.[H-].[Na+].Br[CH:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27]>CN(C)C=O.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[O:17][CH:16]([CH3:19])[C:15](=[O:20])[N:14]([CH:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[C:13]=2[CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 589385588-(2,4-Dimethylphenyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one

生成物 1

HCID 589386018-(2,4-Dimethylphenyl)-2-methyl-4-(1-propylbutyl)-2H-1,4-benzoxazin-3(4H)-one収率 45.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 8-(2,4-dimethylphenyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one (300 mg, 1.12 mmol) in N,N-dimethylformamide (5 ml) was added sodium hydride (43 mg, 1.68 mmol). After the mixture was stirred at 80° C. for 30 min, 4-bromoheptane (804 mg, 4.49 mmol) was added. The mixture was stirred at 80° C. for 18 h and diluted with water. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with 5% ethyl acetate/n-hexane to afford 186 mg (30%) of the title compound.

後処理

  1. stirringThe mixture was stirred at 80° C. for 18 h
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography
  7. washeluting with 5% ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-fda62b9899ae4111a274094088656f75
出典データセット
uspto-grants-2011_03
特許番号
US07897607B2

反応ノート

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