Ammonium sulfamate → Diethyl 5-ethylpyridine-2,3-dicarboxylate

HRID 3918

反応式

HRID 3918 の反応式
[CH3:1][CH2:2][C:3]([CH:5]=O)=[CH2:4].Cl[CH:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].S(=O)(=O)([O-])[NH2:22].[NH4+]>C(O)C>[CH2:2]([C:3]1[CH:4]=[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:22][CH:5]=1)[CH3:1]

参加物

5

反応物 3

HCID 24482Ammonium sulfamateHCID 70203EthylacroleinHCID 10998635Diethyl 2-chloro-3-oxobutanedioate

生成物 1

HCID 10857926Diethyl 5-ethylpyridine-2,3-dicarboxylate収率 86%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A stirred mixture of ethacrolein, (4.2 g, 0.05 mol), diethyl 3-chloro-2-oxo-butanedioate, (11.2 g, 0.05 mol) and ammonium sulfamate, (15.4 g, 0.135 mol) in ethanol (37 mL) is heated at reflux. After 15 hours the mixture is cooled to room temperature and the solvent removed by distillation under reduced pressure. The residue is treated with water and extracted with ethyl acetate. The organic phase is separated and concentrated in vacuo and the residue purified by column chromatography on silica gel using 4:1 hexane-ethyl acetate as the eluent to give 10.8 g (75% yield) of the title product as an oil which is shown to be 95% pure by a gas chromatography assay.

後処理

  1. temperatureis heated
  2. temperatureat reflux
  3. customthe solvent removed by distillation under reduced pressure
  4. additionThe residue is treated with water
  5. extractionextracted with ethyl acetate
  6. customThe organic phase is separated
  7. concentrationconcentrated in vacuo
  8. customthe residue purified by column chromatography on silica gel using 4:1 hexane-ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-b5d15bfc6ae942d6b4900629eb592e0d
出典データセット
uspto-grants-1988_02
特許番号
US04723011

関連ノート

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