Ethyl Acrylate → 3-[N-Dodecyl-N-[2-[4-iodophenoxy]ethyl]amino]propanoic Acid, Ethyl Ester

HRID 1700895Notes

Reaction equation

HRID 1700895 reaction equation
[I:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=1.[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH:25]=[CH2:26]>C(O)C>[CH2:10]([N:9]([CH2:26][CH2:25][C:24]([O:28][CH2:29][CH3:30])=[O:27])[CH2:8][CH2:7][O:6][C:5]1[CH:22]=[CH:23][C:2]([I:1])=[CH:3][CH:4]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 18319005N-2-[4-Iodophenoxy]ethyldodecylamine

Product 1

HCID 573154653-[N-Dodecyl-N-[2-[4-iodophenoxy]ethyl]amino]propanoic Acid, Ethyl EsterYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-2-[4-iodophenoxy]ethyldodecylamine (1.0 g, 2.3 mmol), ethyl acrylate (1.2 g, 12 mmol) and ethanol (3 ml) was stirred and refluxed for 6 h, and then concentrated in vacuo . The residue was chromatographed on silica gel (hexane/ethyl acetate 8:1) to afford the title compound (1.05 g, 86%) as a colorless oil.

Workup

  1. temperaturerefluxed for 6 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on silica gel (hexane/ethyl acetate 8:1)

Sources & evidence

ORD record
ord-2ec6fc2451294ea39f70fbf489ae1668
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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