Dimethylhydantoin → HCID 3028675, compound

HRID 2226163Notes

Reaction equation

HRID 2226163 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]#[CH:18]>C(C(C)=O)C>[CH2:18]([N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7])[C:17]#[CH:16]

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 3028675HCID 3028675, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a stirred solution of 5,5-dimethylhydantoin (10 g, 78 mmole) in methyl ethyl ketone (500 mL) at room temperature was added potassium carbonate (13 g, 94.1 mmole), followed by propargyl bromide (14 g, 80% in toluene, 94.1 mmole). The reaction mixture was then refluxed for 2.5 hr. The mixture was cooled to room temperature and the solid was filtered by suction filtration. The filtrate was concentrated on a rotary evaporator to give 12.5 g (96%) of 3-(2-propynyl)-5,5-dimethylhydantoin as a yellow solid, mp=156°-160° C. An NMR spectrum showed the desired product with a purity about 95%. This intermediate was subjected to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was then refluxed for 2.5 hr
  2. filtrationthe solid was filtered by suction filtration
  3. concentrationThe filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-023363f932584fce805fe0186854a18b
Source dataset
uspto-grants-1994_09
Patent number
US05346913

Reaction notes

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