Diethyl Ether → HCID 57179718, compound

HRID 1164997Notes

Reaction equation

HRID 1164997 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13].C[CH:18]([CH3:25])[C:19]([NH:21][CH2:22][CH2:23][NH2:24])=[O:20].[CH3:26]COCC>CO>[OH:1][CH:2]([CH2:16][NH:24][CH2:23][CH2:22][NH:21][C:19](=[O:20])[CH2:18][CH2:25][CH3:26])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12681828N-(2-Aminoethyl)-2-methylpropanamideHCID 19863749HCID 19863749, compound

Product 1

HCID 57179718HCID 57179718, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.0 g (0.02 mole) of methyl 2-(2,3-epoxypropoxy)-phenylacetate and 2.93 g (0.02 mole) of 2-(2-methylpropionamido)ethylamine in 200 ml of methanol, was heated to reflux for 4 hr. The mixture was concentrated under reduced pressure to afford a dark brown oil which was then stirred with 100 ml of ether for 15 min. to yield an off-white solid. The product was collected by filtration, washed with ether and recrystallized three times from ethyl acetate to provide 0.7 g (9%) of white crystals, which melted at 109°-111° C. The IR and NMR spectra and elemental analysis were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto afford a dark brown oil which
  5. customto yield an off-white solid
  6. filtrationThe product was collected by filtration
  7. washwashed with ether
  8. customrecrystallized three times from ethyl acetate

Sources & evidence

ORD record
ord-b34acfd3759c43deadde7d0ee9cebe70
Source dataset
uspto-grants-1990_03
Patent number
US04906661

Reaction notes

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