Sulfuric Acid → HCID 13730924, compound

HRID 2291791Notes

Reaction equation

HRID 2291791 reaction equation
O[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:12][C:13](=[O:20])[C:14]([CH:17]([CH3:19])[CH3:18])([CH3:16])[N:15]=2)=[N:9][CH:10]=1)([CH3:4])[CH3:3].S(=O)(=O)(O)O.[OH-].[NH4+]>>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:12][C:13](=[O:20])[C:14]([CH:17]([CH3:18])[CH3:19])([CH3:16])[N:15]=2)=[N:9][CH:10]=1)([CH3:4])=[CH2:3]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 13730923HCID 13730923, compound

Product 1

HCID 13730924HCID 13730924, compoundYield 95.5%

Procedure

To 6.4 g of 2-[5-(1-hydroxy-1-methylethyl)-2-pyridyl]-4-isopropyl-4-methyl-2-imidazolin-5-one is added with stirring and cooling (ice) 30 ml concentrated sulfuric acid. The mixture is stirred at room temperature for a further 30 minutes, then poured onto 100 ml ice. The pH of this mixture is adjusted to 4 with concentrated ammonium hydroxide and extracted with 3×200 ml ether. The combined extracts were washed with saturated brine, dried and concentrated to give 5.71 g yellow solid. Recrystallization from ether-hexane gave analytically pure 2-(5-isopropenyl-2-pyridyl)-4-isopropenyl-4-methyl-2-imidazolin-5-one, mp 123°-125° C.

Workup

  1. stirringThe mixture is stirred at room temperature for a further 30 minutes
  2. extractionextracted with 3×200 ml ether
  3. washThe combined extracts were washed with saturated brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af046f8334fd42db8eee0921eb351d22
Source dataset
uspto-grants-1989_01
Patent number
US04798619

Reaction notes

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