Chloroacetaldehyde → 2-(4-Nitrobenzyl)-1,3-thiazole

HRID 30639ノート

反応式

HRID 30639 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[S:13])[NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:15][CH:16]=O.C(=O)([O-])O.[Na+]>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[S:13][CH:15]=[CH:16][N:12]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 27773372-(4-Nitrophenyl)thioacetamide

生成物 1

HCID 692104452-(4-Nitrobenzyl)-1,3-thiazole

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-(4-nitrophenyl)ethanethioamide (0.80 g), chloroacetaldehyde (40% aqueous solution, 2.88 g) and ethanol (20 mL) was heated under reflux for 15 hrs. Saturated aqueous sodium hydrogen carbonate was added to 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, and 2-(4-nitrobenzyl)-1,3-thiazole was obtained as an orange oil (0.35 g, yield 39%) from a fraction eluted with hexane-ethyl acetate (9:1-2:1, v/v).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5c45fcf8d5304f46b253f21eedc39957
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

反応ノート

読み込み中…