Water → 4-[[(6-chloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one

HRID 2390991

反応式

HRID 2390991 の反応式
COC([C:5]1[C:9](=[O:10])[O:8][CH2:7][C:6]=1O)=O.[Cl:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][NH:20][CH3:21])=[CH:15][CH:14]=1.S([O-])(O)(=O)=O.[K+].O>C(#N)CCC.ClCCl>[Cl:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][N:20]([CH3:21])[C:6]2[CH2:7][O:8][C:9](=[O:10])[CH:5]=2)=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 110948836-Chloro-N-methyl-3-pyridinemethanamineHCID 54677706Methyl 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylate

生成物 1

HCID 115504594-[[(6-chloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one収率 105%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8008Butyronitrile溶媒

反応条件

温度
115 °C

実験手順

To a suspension of 18 g of 4-(methoxycarbonyl)-5-oxo-2,5-dihydrofuran-3-ol and 15 g of N-[(6-chloropyridin-3-yl)methyl]methylamine in 210 ml of butyronitrile are added, at room temperature, 16 g of potassium hydrogensulphate. The mixture is stirred at a temperature of 115° C. for 5 hours. Subsequently, the mixture is cooled to room temperature and admixed with 150 ml of water and 70 ml of dichloromethane. The organic phase is removed and the aqueous phase is extracted twice with 70 ml each time of methylene chloride. The combined organic phases are concentrated to dryness. 24 g of 4-[[(6-chloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one are obtained in a purity of 88% (this corresponds to 92% yield).

後処理

  1. additionare added, at room temperature
  2. temperatureSubsequently, the mixture is cooled to room temperature
  3. customThe organic phase is removed
  4. extractionthe aqueous phase is extracted twice with 70 ml each time of methylene chloride
  5. concentrationThe combined organic phases are concentrated to dryness

出典と根拠

ORDレコード
ord-e07d30df71024be7ad1cd76c8ef870c1
出典データセット
uspto-grants-2012_09
特許番号
US08273904B2

関連ノート

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