Methanesulfonic Acid → 2-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole

HRID 30641

反応式

HRID 30641 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:15](OC)(OC)(OC)[CH2:16][CH2:17][CH3:18].CS(O)(=O)=O.O1CCCC1>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][C:15]([CH2:16][CH2:17][CH3:18])=[N:14][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 6395Methanesulfonic AcidHCID 8028TetrahydrofuranHCID 1235121,1,1-TrimethoxybutaneHCID 2873312-(4-Nitrophenyl)acetohydrazide

生成物 1

HCID 692088952-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2-(4-nitrophenyl)acetohydrazide (7.0 g), trimethyl orthobutyrate (16.01 g), methanesulfonic acid (0.69 g) and tetrahydrofuran (200 mL) was heated under reflux for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and 2-(4-nitrobenzyl)-5-propyl-1,3,4-oxadiazole was obtained as a colorless oil (7.73 g, yield 87%) from a fraction eluted with hexane-ethyl acetate (3:2-1:2, v/v).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d3f0feac829549ef83af5f08dda06d3d
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

関連ノート

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