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

HRID 862772

Reaction equation

HRID 862772 reaction equation
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]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 7357802-chloro-N-cyclopropylacetamide

Product 1

HCID 54270018Diethyl [2-(cyclopropylamino)-2-oxoethyl]phosphonateYield 14.7%

Conditions

Temperature
155 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-842f37fd7ead487bbd959ba2af13216c
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Linked notes

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