Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | o-Fluoroacetophenone | HCID 96744 | — |
| Reactant | Ammonium Carbonate | HCID 517111 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | 7248-25-1 | HCID 238123 | 97% |
Reaction Steps
A mixture of freshly distilled 1-(2-fluorophenyl)ethanone (27.6 g, 24.6 ml, 200 mmol, Eq: 1.00), potassium cyanide (15.6 g, 240 mmol, Eq: 1.20), ammonium carbonate (96.1 g, 1.00 mol, Eq: 5.00) and ammonium hydroxide (25%) (130 g, 145 ml, 931 mmol, Eq: 4.65) in ethanol (250 ml) and water (200 ml) was stirred at 60° C. for 5.5 h. The ethanol was removed in vacuum, then cooled to 0° C., cautiously acidified the residue to pH 1, the precipitate was filtered off, washed with dilute HCl and dried at 50° C. first at rotary evaporator, then at high vacuum to give the 5-(2-fluorophenyl)-5-methylimidazolidine-2,4-dione (40.4 g, 194 mmol, 97.0% yield) as a white solid. MS (ISN): m/z=207.5 [M−H]−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09273042B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-25834671b9334a17a652329c0941928d |
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| Source note | uspto-grants-2016_03 |
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