Sodium Hydroxide → 2-(5-Ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonic acid

HRID 2393775Notes

Reaction equation

HRID 2393775 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]([CH2:19]/[CH:20]=[CH:21]/[C:22]([O:24]CC)=[O:23])[C:11](=[O:18])[C:12]([CH:15]([CH3:17])[CH3:16])([CH3:14])[N:13]=2)=[N:7][CH:8]=1)[CH3:2].O1CCCC1.O.[OH-].[Na+]>O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]([CH2:19]/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])[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 14798Sodium HydroxideHCID 21881883Oxolane--water (1/1)HCID 22450183Ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonate

Product 1

HCID 224501892-(5-Ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonate, (E)- (1.16 g, 3.25 mmol) in 1:1 tetrahydrofuran/water is treated with sodium hydroxide (0.45 g, 11.3 mmol) at once. The resulting mixture is stirred at reflux for 1.5 hours, then at room temperature for 16.5 hours. After this period, the reaction mixture is diluted with water, and washed with ether. The aqueous layer is acidified with 1N hydrochloric acid (15 mL), and extracted with ether. The organic extract is dried over sodium sulfate, decolorized with charcoal and vacuum filtered through diatomaceous earth. The filtrate is concentrated in vacuo to give the title product as a yellow solid, mp 53°-58° C.

Workup

  1. temperatureat reflux for 1.5 hours
  2. waitAfter this period
  3. washwashed with ether
  4. extractionextracted with ether
  5. extractionThe organic extract
  6. dry with materialis dried over sodium sulfate
  7. filtrationfiltered through diatomaceous earth
  8. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-7ae6de9ce7914fe297c134e68fa31639
Source dataset
uspto-grants-1998_09
Patent number
US05808079

Reaction notes

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