Sodium Hydroxide → 2-Imidazolidinone, 1-(3-phenyl-2-propenyl)-3-(3-pyridinyl)-, (E)-

HRID 477002Notes

Reaction equation

HRID 477002 reaction equation
[CH2:1]([N:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:11]1=S)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N([O-])=[O:23].[Na+].[OH-].[Na+]>Cl>[CH2:1]([N:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:11]1=[O:23])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14834215(E)-1-cinnamyl-3-(3-pyridyl)imidazolidine-2-thioneHCID 23668193Sodium Nitrite

Product 1

HCID 64507052-Imidazolidinone, 1-(3-phenyl-2-propenyl)-3-(3-pyridinyl)-, (E)-Yield 61%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 3.02 g of (E)-1-cinnamyl-3-(3-pyridyl)imidazolidine-2-thione dissolved in 40 ml of 4N hydrochloric acid, 10 ml of an aqueous solution of 1.03 g of NaNO2 was added dropwise. After stirring at room temperature for 1 hour, the mixture was made alkaline by addition of a sodium hydroxide solution, and the precipitated crystals were collected by filtration. The crystals obtained were washed with water, dried and then purified by silica gel column chromatorgraphy (solvent: chloroform-methanol=30:1), followed by recrystallization from ethanol, to give 1.74 g of (E)-1-cinnamyl-3-(3-pyridyl)-2-imidazolidinone.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customThe crystals obtained
  3. washwere washed with water
  4. customdried
  5. custompurified by silica gel column chromatorgraphy (solvent: chloroform-methanol=30:1)
  6. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-1372568970fc4ddc9948a20a74a257de
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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