Propargyl bromide → HCID 18966554, compound

HRID 2226167Notes

Reaction equation

HRID 2226167 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11]([CH3:15])([CH3:14])[NH:10][C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]#[CH:25].C(OCC)(=O)C.CCCCCC>CC(C)=O>[CH2:1]([N:8]1[C:12](=[O:13])[C:11]([CH3:14])([CH3:15])[N:10]([CH2:25][C:24]#[CH:23])[C:9]1=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 141912Hydantoin, 3-benzyl-5,5-dimethyl-HCID 21226206Ethyl acetate hexane

Product 1

HCID 18966554HCID 18966554, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-benzyl-5,5-dimethylhydantoin (9.5 g, 43.6 mmole) in acetone (100 mL) at room temperature were added potassium carbonate (8.4 g, 60.9 mmole) and propargyl bromide (7.1 g of 80 % in toluene, 47.7 mmole). The reaction mixture was refluxed for 16 hr; cooled to room temperature and the solid was filtered off by suction-filtration. The filtrate was concentrated and the resultant residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate. After evaporation, a yellow crude oil was obtained. A pure product, 5.5 g (yield=50%) of 3-benzyl-1-propargyl-5,5-dimethylhydantoin as a yellow oil, was obtained by column chromatography on silica gel eluting with ethyl acetate:hexane (1:1 ).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hr
  2. filtrationthe solid was filtered off by suction-filtration
  3. concentrationThe filtrate was concentrated
  4. additionthe resultant residue was diluted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customAfter evaporation
  8. customa yellow crude oil was obtained

Sources & evidence

ORD record
ord-07279795d5ec4cce9a1eec7f119f060a
Source dataset
uspto-grants-1994_09
Patent number
US05346913

Reaction notes

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