Potassium Cyanide → 7248-25-1

HRID 920138Notes

Reaction equation

HRID 920138 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH3:9].[C-:11]#[N:12].[K+].[C:14](=[O:17])([O-])[O-].[NH4+:18].[NH4+].[OH-:20].[NH4+]>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH3:9])[NH:18][C:11](=[O:20])[NH:12][C:14]1=[O:17]

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 96744o-FluoroacetophenoneHCID 517111Ammonium Carbonate

Product 1

HCID 2381237248-25-1Yield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

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]−.

Workup

  1. customThe ethanol was removed in vacuum
  2. temperaturecooled to 0° C.
  3. filtrationthe precipitate was filtered off
  4. washwashed with dilute HCl
  5. customdried at 50° C. first at rotary evaporator

Sources & evidence

ORD record
ord-25834671b9334a17a652329c0941928d
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

Loading…