Triethyl phosphite → Diethyl [2-(cyclopropylamino)-2-oxoethyl]phosphonate

HRID 862772

Reaktionsgleichung

Reaktionsgleichung von HRID 862772
Cl[CH2:2][C:3]([NH:5][CH:6]1[CH2:8][CH2:7]1)=[O:4].[P:9]([O:16]CC)([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>>[CH2:11]([O:10][P:9]([CH2:2][C:3](=[O:4])[NH:5][CH:6]1[CH2:8][CH2:7]1)(=[O:16])[O:13][CH2:14][CH3:15])[CH3:12]

Komponenten

3

Edukt 2

HCID 31215Triethyl phosphiteHCID 7357802-chloro-N-cyclopropylacetamide

Produkt 1

HCID 54270018Diethyl [2-(cyclopropylamino)-2-oxoethyl]phosphonateAusbeute 14,7 %

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

2-Chloro-N-cyclopropylacetamide (20 g, 0.15 moles) was added in portions with stirring to triethyl phosphite (28 g, 0.17 moles, Aldrich) at 110° C. The solution was then heated to 155° C. for 30 minutes, cooled to 125° C., and the volatiles were removed by distillation under aspirator vacuum (15 mm Hg) at this temperature. The residual oil was stirred with pentane (200 mL) while cooling in an ice bath to induce crystallization. Filtration gave 5.2 g (14%) of diethyl((cyclopropylcarbamoyl)methyl)phosphonate as white crystals; m.p. 51°-56° C. The liquor was concentrated and cooled to give 25.3 g (71%) of a second crop; m.p. 50°-56° C. Recrystallization from dichloromethane/hexanes gave the analytical sample, m.p. 55°-57° C.

Aufarbeitung

  1. temperaturecooled to 125° C.
  2. customthe volatiles were removed by distillation under aspirator vacuum (15 mm Hg) at this temperature
  3. temperaturewhile cooling in an ice bath
  4. customcrystallization
  5. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-842f37fd7ead487bbd959ba2af13216c
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719186

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