碘化钾 → N-butyl-3,3-bis(diethoxyphosphinyl)propionamide

HRID 1972

反应方程式

HRID 1972 反应方程式
[CH2:1]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[P:2](=[O:9])([O:6][CH2:7][CH3:8])[O:3][CH2:4][CH3:5].[H-].[Na+].[H-].[CH2:21]([NH:25][C:26](=[O:29])[CH2:27]Cl)[CH2:22][CH2:23][CH3:24].[I-].[K+].[Cl-].[Na+]>C1COCC1>[CH2:21]([NH:25][C:26](=[O:29])[CH2:27][CH:1]([P:2]([O:6][CH2:7][CH3:8])([O:3][CH2:4][CH3:5])=[O:9])[P:10]([O:11][CH2:12][CH3:13])([O:14][CH2:15][CH3:16])=[O:17])[CH2:22][CH2:23][CH3:24]

参与物

8

反应物 6

HCID 4875碘化钾HCID 5234Halite (NaCl)HCID 15455四乙基亚甲基二磷酸脂HCID 24758氢化钠HCID 166653HydrideHCID 219645N-丁基-2-氯乙酰胺

产物 1

HCID 19689044N-butyl-3,3-bis(diethoxyphosphinyl)propionamide收率 70%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂3 次

实验过程

Tetraethyl methylenebisphosphonate (1.44 g, 5.0 mmol) in THF (1 mL) was added to a slurry of 80% sodium hydride (150 mg, 5.0 mmol) in THF (4 mL) at 0° C. The reaction was warmed to room temperature and stirred until all of the hydride was consumed. A solution of N-butyl-2-chloroacetamide (0.75 g, 5.0 mmol) in THF (1 ml) and potassium iodide (100 mg) were then added. The reaction mixture was then heated at 50° C. for 18 hours, during which time sodium chloride precipitated. Additional sodium hydride (20 mg) was added, and the reaction mixture was heated an additional 4 hours. After cooling, the mixture was poured into 1N HCl (10 mL) and diethyl ether (50 mL) was added. The diethyl ether layer was further extracted with water (3×10 mL). The combined aqueous fractions were extracted with dichloromethane (4×25 mL). The combined extracts were dried (Na2SO4) and concentrated to give the title compound (1.40 g, 70%) as an oil.

后处理

  1. customwas consumed
  2. customprecipitated
  3. additionAdditional sodium hydride (20 mg) was added
  4. temperaturethe reaction mixture was heated an additional 4 hours
  5. temperatureAfter cooling
  6. additionthe mixture was poured into 1N HCl (10 mL) and diethyl ether (50 mL)
  7. additionwas added
  8. extractionThe diethyl ether layer was further extracted with water (3×10 mL)
  9. extractionThe combined aqueous fractions were extracted with dichloromethane (4×25 mL)
  10. dry with materialThe combined extracts were dried (Na2SO4)
  11. concentrationconcentrated

来源与证据

ORD记录
ord-0d06fa7cb400433aac9523d5cb4e75c0
来源数据集
uspto-grants-1998_03
专利号
US05728650

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