Hydrochloric Acid → 5-Ethyl-2-pyridyl-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetic acid

HRID 1938510Notes

Reaction equation

HRID 1938510 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]([CH2:19][C:20]([O:22]CC)=[O:21])[C:11](=[O:18])[C:12]([CH:15]([CH3:17])[CH3:16])([CH3:14])[N:13]=2)=[N:7][CH:8]=1)[CH3:2].[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]([CH2:19][C:20]([OH:22])=[O:21])[C:11](=[O:18])[C:12]([CH:15]([CH3:17])[CH3:16])([CH3:14])[N:13]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22450190Ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetate

Product 1

HCID 224501785-Ethyl-2-pyridyl-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetate (2.12 g, 6.41 mmol) in tetrahydrofuran is treated with 2N sodium hydroxide (8 mL). The resulting mixture is stirred at room temperature for 16 hours. After this period, the reaction mixture is concentrated in vacuo to obtain a residue. The residue is acidified with concentrated hydrochloric acid and then extracted with ether. The organic extract is dried over magnesium sulfate, vacuum filtered through diatomaceous earth and concentrated in vacuo to give the title product as a white solid, mp 134°-136° C.

Workup

  1. waitAfter this period
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. customto obtain a residue
  4. extractionextracted with ether
  5. extractionThe organic extract
  6. dry with materialis dried over magnesium sulfate, vacuum
  7. filtrationfiltered through diatomaceous earth
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-071023308b4146eeb58bed47fce085d5
Source dataset
uspto-grants-1997_12
Patent number
US05693658

Reaction notes

Loading…