2-Pyrrolidone → N-[2,2-Dimethoxyethyl]-3-[2-oxopyrrolidin-1-yl]propionamide

HRID 1584516Notes

Reaction equation

HRID 1584516 reaction equation
[CH3:1][O:2][CH:3]([O:10][CH3:11])[CH2:4][NH:5][C:6](=[O:9])[CH:7]=[CH2:8].[NH:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17]>>[CH3:1][O:2][CH:3]([O:10][CH3:11])[CH2:4][NH:5][C:6](=[O:9])[CH2:7][CH2:8][N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17]

Participants

3

Reactant 2

HCID 120252-PyrrolidoneHCID 9898899N-(2,2-Dimethoxyethyl)-2-propenamide

Product 1

HCID 21182207N-[2,2-Dimethoxyethyl]-3-[2-oxopyrrolidin-1-yl]propionamide

Conditions

Temperature
80 °C

Procedure

10 g (62.8 mmol) of the acrylamido acetal from Example 2 are mixed with 6 g (70.5 mmol) of pyrrolidone and, after addition of one drop of Triton B, the mixture is warmed to 80° C. After 10 minutes, the reaction is terminated. The thin-layer chromatogram shows no UV absorbing acetal. The product is subsequently freed from traces of solvent under a high vacuum. It is a single compound according to TLC. NMR data: 2 methylene protons at each of 2.0, 2.4, 2.5, 3.3, 3.4 and 3.6 ppm(t), 6 methoxy protons at 3.35 ppm(s), 1 acetal proton at 4.4 ppm(t), 1 amide proton at 7.2 ppm. ##STR41##

Workup

  1. additionafter addition of one drop of Triton B
  2. customthe reaction is terminated
  3. customabsorbing acetal

Sources & evidence

ORD record
ord-7d280dbafee24fbb800a23d1f7c17469
Source dataset
uspto-grants-1999_08
Patent number
US05932674

Reaction notes

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