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

HRID 862772

反応式

HRID 862772 の反応式
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]

参加物

3

反応物 2

HCID 31215Triethyl phosphiteHCID 7357802-chloro-N-cyclopropylacetamide

生成物 1

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

反応条件

温度
155 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-842f37fd7ead487bbd959ba2af13216c
出典データセット
uspto-grants-1998_02
特許番号
US05719186

関連ノート

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