Nitrogen → HCID 66817208, compound

HRID 1755043Notes

Reaction equation

HRID 1755043 reaction equation
[CH:1]([B-](F)(F)F)=[CH2:2].[K+].C(N(C(C)C)C(C)C)C.Br[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28](=[O:29])[CH2:27][NH:26][C:25]2=[O:30])=[CH:20][C:19]=1[CH3:31].N#N>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH3:31][C:19]1[CH:20]=[C:21]([N:24]2[C:28](=[O:29])[CH2:27][NH:26][C:25]2=[O:30])[CH:22]=[CH:23][C:18]=1[CH:1]=[CH2:2]

Participants

7

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 66817913HCID 66817913, compound

Product 1

HCID 66817208HCID 66817208, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

Potassium vinyltrifluoroborate (356 mg, 242 μmol), ethyldiisopropylamine (48 μL, 279 μmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane adduct (15.1 mg, 18.6 μmol) were added to a solution of 3-(4-bromo-3-methyl-phenyl)-imidazolidine-2,4-dione (50 mg, 186 μmol) in n-PrOH (372 μL) at room temperature in an N2 atmosphere. The mixture was stirred at 100° C. for 1.5 hours, and the reaction solution was then cooled. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 3-(3-methyl-4-vinyl-phenyl)-imidazolidine-2,4-dione as a yellow brown form (33 mg, 82%).

Workup

  1. temperaturethe reaction solution was then cooled
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-0ee1074a080a49e88de875a58a07ff28
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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