Sodium hydride → 1-(3,3-Diethoxypropyl)tetrahydropyrimidin-2-one

HRID 10188

반응식

HRID 10188 반응식
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][CH2:6][NH2:7])[CH3:2].Cl[CH2:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17].[H-].[Na+]>C(OCC)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][CH2:6][N:7]1[CH2:12][CH2:13][CH2:14][NH:15][C:16]1=[O:17])[CH3:2]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 166752Propane, 1-chloro-3-isocyanato-HCID 5210291-Amino-3,3-diethoxypropane

생성물 1

HCID 692247861-(3,3-Diethoxypropyl)tetrahydropyrimidin-2-one수율 98.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a stirred and ice-cooled solution of 3-aminopropionaldehyde diethylacetal (5.88 g, 40 mmole) in diethyl ether (35 mL) was added dropwise 3-chloropropyl isocyanate (4.78 g, 40 mmole). The reaction mixture was stirred at room temperature for 4 hours. The mixture was concentrated and dissolved in N,N-dimethylformamide (40 mL). To this solution was added de-oiled sodium hydride (0.96 g, 40 mmole). The reaction mixture was stirred at 70° C. for 18 hours, concentrated, taken up in diethyl ether (40 mL), and filtered. The filtrate was concentrated and purified by silica gel chromatography, eluting with hexane-ethyl acetate-methanol (10:9.7:0.3), gave 1-(3,3-diethoxypropyl)-tetrahydropyrimidin-2-one (9.05 g) as an oil.

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 4 hours
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in N,N-dimethylformamide (40 mL)
  4. stirringThe reaction mixture was stirred at 70° C. for 18 hours
  5. concentrationconcentrated
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel chromatography
  9. washeluting with hexane-ethyl acetate-methanol (10:9.7:0.3)

출처 및 근거

ORD 기록
ord-116343ab6f52409da190df2d18211306
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094778B2

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