Ethanol → 5-Methyl-5-(pyridin-4-yl)imidazolidine-2,4-dione

HRID 1245324Notes

Reaction equation

HRID 1245324 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[C-:10]#[N:11].[K+].[NH4+:13].[OH-:14].C[CH2:16][OH:17]>>[CH3:2][C:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)[NH:13][C:10](=[O:14])[NH:11][C:16]1=[O:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 142824-AcetylpyridineHCID 14923Ammonium Hydroxide

Product 1

HCID 2227025-Methyl-5-(pyridin-4-yl)imidazolidine-2,4-dione

Conditions

Temperature
60 °C

Procedure

A mixture of 4-acetyl pyridine (3.0 mL), NH4HCO3 (7.73 g), KCN (2.16 g), and concentrated NH4OH (8.2 mL) in EtOH (10.35 mL) was heated to 60° C. overnight under a reflux condenser. The reaction mixture was extracted with ether, then acidified to pH 4.5 with concentrated HCl and extracted with EtOAc. The combined organic extracts from the acidic extraction were dried over Na2SO4. Solvent was removed in vacuo to yield crude 5-methyl-5-(4-pyridyl)-imidazolidinedione as an off-white solid.

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. extractionextracted with EtOAc
  3. extractionThe combined organic extracts from the acidic extraction
  4. dry with materialwere dried over Na2SO4
  5. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-340defd244444dcfac925803ca7035ad
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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