Sodium hydride → 3-(4-Tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

HRID 546583Notes

Reaction equation

HRID 546583 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:14]2=[O:21])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[Cl:22][C:23]1[CH:28]=[C:27]([CH2:29]Cl)[CH:26]=[CH:25][N:24]=1>CN(C)C=O.O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15]([CH2:29][C:27]3[CH:26]=[CH:25][N:24]=[C:23]([Cl:22])[CH:28]=3)[C:14]2=[O:21])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 576259723-(4-Tert-butylphenyl)-5,5-dimethyl-imidazolidine-2,4-dione

Product 1

HCID 576259713-(4-Tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dioneYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1.1 g of sodium hydride in 40 mL of dimethylformamide under argon are successively added 4.9 g of 3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione obtained in stage c) of Example 1 and 4.55 g of 2-chloro-4-(chloromethyl)pyridine. The reaction mixture is stirred for 48 hours at room temperature and then diluted with 260 mL of water. The solid formed is filtered off, rinsed with diisopropyl ether and dried to give 4.61 g of 3-(4-tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione in the form of a beige-coloured powder, the characteristics of which are as follows:

Workup

  1. customThe solid formed
  2. filtrationis filtered off
  3. washrinsed with diisopropyl ether
  4. customdried

Sources & evidence

ORD record
ord-7c53bd76a9bd4d68940eca962bf2a48f
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

Loading…