Water → Benzyl [2-(dimethylcarbamoyl)ethyl]methylcarbamate

HRID 17415

Reaktionsgleichung

Reaktionsgleichung von HRID 17415
[CH3:1][N:2]([CH3:18])[C:3]([CH2:5][CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4].[H-].[Na+].I[CH3:22].O>O1CCCC1>[CH3:18][N:2]([CH3:1])[C:3]([CH2:5][CH2:6][N:7]([CH3:22])[C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19971000Benzyl [2-(dimethylcarbamoyl)ethyl]carbamate

Produkt 1

HCID 69194413Benzyl [2-(dimethylcarbamoyl)ethyl]methylcarbamateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Benzyl [2-(dimethylcarbamoyl)ethyl]carbamate (I-139) (0.69 g, 2.76 mmol) was dissolved in tetrahydrofuran (10 ml), and with cooling with ice, sodium hydride (oily, about 55%, 0.15 g, 3.44 mmol) was added, followed by stirring for 10 minutes. Iodomethane (0.26 ml, 4.18 mmol) was added, followed by stirring at room temperature for 18 hours, and water was added. After extraction with ethyl acetate and drying over anhydrous sodium sulfate, the solvent was evaporated away, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1) to obtain a colorless oil (0.63 g, 86%).

Aufarbeitung

  1. additionwas added
  2. stirringby stirring at room temperature for 18 hours
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customthe solvent was evaporated away
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-530b116b529646a3ad038a0a1c9fd348
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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