Propanethioamide → Methyl 2-ethyl-5-methyl-1,3-thiazole-4-carboxylate

HRID 2221701ノート

反応式

HRID 2221701 の反応式
Br[CH:2]([CH3:9])[C:3](=O)[C:4]([O:6][CH3:7])=[O:5].[C:10](=[S:14])([NH2:13])[CH2:11][CH3:12]>C(O)C>[CH2:11]([C:10]1[S:14][C:2]([CH3:9])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[N:13]=1)[CH3:12]

参加物

4

反応物 2

HCID 2760628PropanethioamideHCID 11183175Methyl 3-bromo-2-oxobutanoate

生成物 1

HCID 23076482Methyl 2-ethyl-5-methyl-1,3-thiazole-4-carboxylate収率 53%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of methyl 3-bromo-2-oxobutanoate (16.2 g), propanethioamide (7.4 g) and ethanol (150 mL) was heated under reflux for 3 hrs. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:4, v/v) to give methyl 2-ethyl-5-methyl-1,3-thiazole-4-carboxylate as a yellow oil (8.1 g, yield 53%).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hrs
  3. customThe solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. washeluted with ethyl acetate-hexane (1:4, v/v)

出典と根拠

ORDレコード
ord-bbc1ef9f484a407aa13b9d21be20f75e
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

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