Water → HCID 11043435, compound

HRID 2226993Notes

Reaction equation

HRID 2226993 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][NH:12][C:11]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CS(O[CH2:24][C:25]#[CH:26])(=O)=O.O>C(C(C)=O)C(C)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][N:12]([CH2:26][C:25]#[CH:24])[C:11]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 305925propargyl mesylateHCID 10857002HCID 10857002, compound

Product 1

HCID 11043435HCID 11043435, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

In 8 ml of methyl isobutyl ketone were dissolved 500 mg (2.27 mmoles) of 3-benzyloxymethyl-imidazolidine-2,4-dione and 37 mg (0.115 mmoles) of tetrabutylammonium bromide followed by addition of 114 mg (2.85 mmoles) of sodium hydroxide at room temperature with stirring. Thereafter, 610 mg (4.55 mmoles) of propargyl methanesulfonate was added dropwise at room temperature with stirring and the mixture was further stirred at room temperature for 7 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution in that order, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate =3:1) to give 461 mg (1.78 mmoles) of 3-benzyloxymethyl-l-propargylimidazolidine-2,4-dione.

Workup

  1. stirringwith stirring
  2. stirringthe mixture was further stirred at room temperature for 7 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride solution in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dbc2615f58d44781baecb41b7030fb27
Source dataset
uspto-grants-1994_09
Patent number
US05350859

Reaction notes

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