Ethanol → 5-(2H-1,3-benzodioxol-5-yl)-5-methylimidazolidine-2,4-dione

HRID 1690139Notes

Reaction equation

HRID 1690139 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH3:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[C-]#N.[Na+].[C:16](=[O:19])([O-])[O-].[NH4+:20].[NH4+:21].[CH2:22]([OH:24])C>O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH3:11])[NH:21][C:22](=[O:24])[NH:20][C:16]3=[O:19])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 76622AcetopiperoneHCID 517111Ammonium Carbonate

Product 1

HCID 28298175-(2H-1,3-benzodioxol-5-yl)-5-methylimidazolidine-2,4-dioneYield 51.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

1-(Benzo[d][1,3]dioxol-5-yl)ethanone (446 mg, 2.72 mmol) was dissolved in ethanol (200 mL) and water (200 mL). The resultant mixture was added with sodium cyanide (200 mg, 4.08 mmol) and ammonium carbonate (918 mg, 9.55 mmol) and stirred at 70° C. overnight. The reaction solution was filtered, washed with water and hexane/ethyl acetate, and dried using anhydrous sodium sulfate. 5-(Benzo[d][1,3]dioxol-5-yl)-5-methylimidazolidine-2,4-dione (326 mg, yield 51.2%) was obtained as a white crystal.

Workup

  1. filtrationThe reaction solution was filtered
  2. washwashed with water and hexane/ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-3bcc735f10a843489e21e51f5628df24
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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