Triethylamine → HCID 21472661, compound

HRID 2396907Notes

Reaction equation

HRID 2396907 reaction equation
[NH2:1][CH2:2][CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].C(N(CC)CC)C.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1>ClCCl>[CH2:9]([O:8][P:4]([CH2:3][CH2:2][NH:1][C:20]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[O:27])([O:5][CH2:6][CH3:7])=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 2733596Diethyl (2-aminoethyl)phosphonate

Product 1

HCID 21472661HCID 21472661, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of diethyl 2-aminoethylphosphonate (8.1 g), triethylamine (9.1 g) and dichloromethane (100 ml) at 5° C. was added nicotinic acid chloride hydrochloride (10.4 g) in small portions over a period of 15 minutes. After being stirred for additional 1.5 hours, the reaction mixture was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (10% methanol in chloroform) to give 11.2 g of N-(2-diethoxyphosphoryl-ethyl)-3-pyridinecarboxamide as an oil.

Workup

  1. washthe reaction mixture was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel (10% methanol in chloroform)

Sources & evidence

ORD record
ord-7eb6bfd8b6474dc4a29e4e8e17faccfe
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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