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

HRID 862772

반응식

HRID 862772 반응식
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]

참가 물질

3

반응물 2

HCID 31215Triethyl phosphiteHCID 7357802-chloro-N-cyclopropylacetamide

생성물 1

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

반응 조건

온도
155 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-842f37fd7ead487bbd959ba2af13216c
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719186

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