Sodium Hydroxide → HCID 90224863, compound

HRID 1487090Notes

Reaction equation

HRID 1487090 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=O)=[CH:4][C:3]=1[CH3:16].[O-:17][C:18]#[N:19].[Na+].C(=O)([O-])O.[Na+].[OH-].[Na+]>ClCCl.C(O)(=O)C>[Br:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([N:9]2[C:10]([CH3:15])([CH3:14])[C:11](=[O:13])[NH:19][C:18]2=[O:17])=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 90224886HCID 90224886, compound

Product 1

HCID 90224863HCID 90224863, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-((4-bromo-3,5-dimethylphenyl)amino)-2-methyl propanoic acid (5.79 g of the compound obtained from Reaction 1-1) in dichloromethane (62 mL) and acetic acid (62 mL), sodium cyanate (5.03 g, 59.8 mmol) was added at room temperature. The mixture was stirred at room temperature for three hours. A saturated solution of sodium hydrogen carbonate (400 mL) was added to adjust the pH to 7-8 using a 5 N aqueous sodium hydroxide, and this mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained solid was washed sequentially with ethyl acetate-hexane and then with dichloromethane-hexane to obtain 1-(4-bromo-3,5-dimethylphenyl)-5,5-dimethylimidazolidine-2,4-dione (3.80 g, 66%).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe obtained solid was washed sequentially with ethyl acetate-hexane

Sources & evidence

ORD record
ord-c2e5903d2f3a4589990246a9e4042efd
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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