Water → HCID 66817495, compound

HRID 1754971Notes

Reaction equation

HRID 1754971 reaction equation
CO[C:3](=[O:8])[C:4]([NH2:7])([CH3:6])[CH3:5].C(N(CC)C(C)C)(C)C.[Br:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([NH:26][C:27](=O)[O:28]C)=[CH:21][C:20]=1[CH3:31].O>CC(N(C)C)=O>[Br:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([N:26]2[C:3](=[O:8])[C:4]([CH3:5])([CH3:6])[NH:7][C:27]2=[O:28])=[CH:21][C:20]=1[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 4186341Methyl 2-amino-2-methylpropanoateHCID 66827417HCID 66827417, compound

Product 1

HCID 66817495HCID 66817495, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

α-Aminoisobutyric acid methyl ester (3.2 g, 20.92 mmol) and N,N-diisopropylethylamine (6.1 ml, 34.86 mmol) were added to a solution of methyl (4-bromo-3,5-dimethylphenyl)carbamate (900 mg, 3.48 mmol) in anhydrous DMA (17.5 ml, 0.2 M). After irradiation with microwaves at 170° C. for 30 minutes, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic phase was sequentially washed with water and saturated brine and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3-(4-bromo-3,5-dimethylphenyl)-5,5-dimethylimidazolidine-2,4-dione (304 mg, 28%)

Workup

  1. customAfter irradiation with microwaves at 170° C. for 30 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic phase was sequentially washed with water and saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8785af498ea44997be3304b5fa658e7b
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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