Methyl iodide → 5-Benzyl-3-n-butyl-1-methylhydantoin

HRID 847728Notes

Reaction equation

HRID 847728 reaction equation
[CH2:1]([CH:8]1[NH:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][CH3:17])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:22]>CN(C)C=O>[CH2:1]([CH:8]1[N:12]([CH3:22])[C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][CH3:17])[C:9]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3591483-Butyl-5-(phenylmethyl)-2,4-imidazolidinedione

Product 1

HCID 127907495-Benzyl-3-n-butyl-1-methylhydantoinYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

5-Benzyl-3-n-butyl hydantoin (7.38 g, 0.03 mole) was dissolved in dimethylformamide (50 ml.) and added dropwise with stirring to a suspension of sodium hydride (1.44 g. 50% oil dispersion) in dimethylformamide (20 ml). When gassing ceased, iodomethane (2 ml) was added and the mixture warmed to 50° C. and maintained at 50° C. for 5 hours. The mixture was poured into ice/water (500 ml) and extracted with ether. The ether extract was evaporated in vacuo to give a colourless oil which failed to crystallise and was distilled in a Kugelrohr apparatus to give the title compound (6.6 g; 85%) b.p. 145° C./0.02 mm.

Workup

  1. additionadded dropwise
  2. temperaturemaintained at 50° C. for 5 hours
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. customwas evaporated in vacuo
  6. customto give a colourless oil which
  7. customto crystallise
  8. distillationwas distilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-40f1712659d04956a0f03cbd49efcbe5
Source dataset
uspto-grants-1981_10
Patent number
US04293563

Reaction notes

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