Propargyl bromide → HCID 18966549, compound

HRID 2226165Notes

Reaction equation

HRID 2226165 reaction equation
[CH2:1]([N:4]1[C:8](=[O:9])[C:7]([CH3:11])([CH3:10])[NH:6][C:5]1=[O:12])[C:2]#[CH:3].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]#[CH:21]>C(C(C)=O)C.O>[CH2:21]([N:6]1[C:7]([CH3:10])([CH3:11])[C:8](=[O:9])[N:4]([CH2:1][C:2]#[CH:3])[C:5]1=[O:12])[C:20]#[CH:19]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 3028675HCID 3028675, compound

Product 1

HCID 18966549HCID 18966549, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a stirred solution of 3-(2-propynyl)-5,5-dimethylhydantoin (3 g, 18.1 mmole) in methyl ethyl ketone (125 mL) at room temperature was added K2CO3 (2.8 g, 20.3 mmole), followed by propargyl bromide (3 g, 80% in toluene, 20.2 mmole). The reaction mixture was then refluxed for 24 hr. The reaction mixture was cooled to room temperature and was diluted with water and extracted with methylene chloride (3×125 mL). The organic layer was washed with saturated NaCl and dried over MgSO4. Evaporation of the volatiles yielded 3.3 g (89 %) of 1,3-di-propargyl-5,5-dimethylhydantoin as a light yellow semi-solid. An NMR spectrum showed the desired structure. This intermediate was subjected to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was then refluxed for 24 hr
  2. extractionextracted with methylene chloride (3×125 mL)
  3. washThe organic layer was washed with saturated NaCl
  4. dry with materialdried over MgSO4
  5. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-2b18fe3bf8404e2fa55c9b3e9b7b1a23
Source dataset
uspto-grants-1994_09
Patent number
US05346913

Reaction notes

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