Ethanol → Benzylsulfanylmethyl-5-cyclopropyl-imidazolidine-2,4-dione

HRID 1441502Notes

Reaction equation

HRID 1441502 reaction equation
[CH2:1]([S:8][CH2:9]C(C1CC1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[C:18](=[O:21])([O-])[O-].[NH4+:22].[NH4+:23].[CH3:24][C:25](OC)([CH3:27])C.[CH2:30]([OH:32])[CH3:31]>O>[CH3:5][CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1].[CH2:1]([S:8][CH2:9][N:22]1[CH:31]([CH:27]2[CH2:24][CH2:25]2)[C:30](=[O:32])[NH:23][C:18]1=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 702EthanolHCID 8929Sodium CyanideHCID 15413tert-Butyl methyl etherHCID 517111Ammonium CarbonateHCID 63905673HCID 63905673, compound

Product 2

HCID 78922-MethylpentaneHCID 66734956Benzylsulfanylmethyl-5-cyclopropyl-imidazolidine-2,4-dioneYield 32.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2-Benzylsulfanyl-1-cyclopropyl-ethanone (27.55 g, 0.133 mol) was dissolved in ethanol (250 ml) and dispensed into 20×40 ml vials. Sodium cyanide (6.52 g, 0.133 mol) and ammonium carbonate (64 g, 0.667 mol) were dissolved in water (250 ml) and divided into the vials, which were then sealed and heated at 90° C. for 5 h behind a safety screen. After cooling to room temperature, the contents of the vials were combined, TBME was added, and the mixture was washed with water (×2), brine (×1), and then dried over sodium sulphate. Evaporation then gave the crude product (16.5 g, 45%). This material was absorbed onto silica and chromatographed (5×9.5 cm column of silica) eluting with iso-hexane to 50% ethyl acetate:iso-hexane to yield the title compound (11.81 g, 32.1%).

Workup

  1. customwere then sealed
  2. temperatureAfter cooling to room temperature
  3. washthe mixture was washed with water (×2), brine (×1)
  4. dry with materialdried over sodium sulphate
  5. customEvaporation
  6. customthen gave the crude product (16.5 g, 45%)
  7. customThis material was absorbed onto silica
  8. customchromatographed (5×9.5 cm column of silica)
  9. washeluting with iso-hexane to 50% ethyl acetate

Sources & evidence

ORD record
ord-645ad512b6504166b683bdff146d5ff8
Source dataset
uspto-grants-2010_02
Patent number
US07655664B2

Reaction notes

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