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

HRID 2390991

반응식

HRID 2390991 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8008Butyronitrile용매

반응 조건

온도
115 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e07d30df71024be7ad1cd76c8ef870c1
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273904B2

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