Dimethylformamide → 3-methyl-5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one

HRID 30668ノート

反応式

HRID 30668 の反応式
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[O:13][C:12](=[O:14])[NH:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].IC.[CH3:19]N(C)C=O.[H-].[Na+]>O>[CH3:19][N:11]1[N:10]=[C:9]([CH2:8][C:7]2[CH:15]=[CH:16][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[O:13][C:12]1=[O:14]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 218227135-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one

生成物 1

HCID 218134333-methyl-5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one収率 71%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one (1.0 g), iodomethane (0.97 g) and N,N-dimethylformamide (30 mL) was added sodium hydride (60% in oil, 0.20 g) at room temperature. The reaction mixture was stirred at room temperature for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 3-methyl-5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one as colorless crystals (0.75 g, yield 71%) from a fraction eluted with hexane-ethyl acetate (3:1-2:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-1f863b11ca6549b9894b65617e04ced5
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

反応ノート

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