Benzyl Bromide → N-ethyl-3-benzyloxy-4-nitrobenzamide

HRID 1717356ノート

反応式

HRID 1717356 の反応式
[CH2:1]([NH:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([OH:14])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.C(=O)([O-])O.[Na+]>[CH2:1]([NH:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([O:14][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1)[CH3:2]

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21029708N-ethyl-3-hydroxy-4-nitrobenzamide

生成物 1

HCID 58637381N-ethyl-3-benzyloxy-4-nitrobenzamide収率 72.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

N-Ethyl-3-hydroxy-4-nitrobenzamide (5.23 g, 24.9 mmol) obtained in Example 312a) was dissolved in anhydrous DMF (100 ml), potassium carbonate (4.47 g, 32.3 mmol, 1.3 eq.) was added at room temperature, benzyl bromide (3.17 ml, 26.1 mmol, 1.05 eq.) was added dropwise, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with 5% aqueous sodium hydrogen carbonate solution (200 ml) and extracted with ethyl acetate-hexane (3:1, 200 ml and 150 ml). The organic layer was washed sequentially with 5% aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated, and diethyl ether was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a yellow powder (5.42 g, 18.1 mmol, 72.5%).

後処理

  1. extractionextracted with ethyl acetate-hexane (3:1, 200 ml and 150 ml)
  2. washThe organic layer was washed sequentially with 5% aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additiondiethyl ether was added to the residue
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with diethyl ether
  8. customdried

出典と根拠

ORDレコード
ord-8b57f31f9a6c4aedaf445edd95333ad9
出典データセット
uspto-grants-2010_09
特許番号
US07803822B2

反応ノート

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