Dimethylformamide → 3-Methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]imidazolidine-2,4-dione

HRID 2281045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2281045
[B:1]1([C:10]2[CH:15]=[CH:14][C:13]([CH2:16]Br)=[CH:12][CH:11]=2)[O:5][C:4]([CH3:7])([CH3:6])[C:3]([CH3:9])([CH3:8])[O:2]1.[CH3:18][N:19]1[C:23](=[O:24])[CH2:22][NH:21][C:20]1=[O:25].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH3:18][N:19]1[C:23](=[O:24])[CH2:22][N:21]([CH2:16][C:13]2[CH:14]=[CH:15][C:10]([B:1]3[O:5][C:4]([CH3:7])([CH3:6])[C:3]([CH3:9])([CH3:8])[O:2]3)=[CH:11][CH:12]=2)[C:20]1=[O:25]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1388512,4-Imidazolidinedione, 3-methyl-HCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 671722823-Methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]imidazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

2-[4-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaboronate (5.00 g, 16.84 mmol), 3-methylimidazolidine-2,4-dione (2.11 g, 18.52 mmol, 1.1 equiv) and potassium carbonate (4.65 g, 33.7 mmol, 2 equiv) were combined and treated with N,N-dimethylformamide (17 mL). The mixture heated for 3 hours at 45° C., cooled to ambient temperature, diluted with ethyl acetate and washed with water (3×) and brine. The organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo to afford the titled compound.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. washwashed with water (3×) and brine
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-99778bbd385a450dad128757ba515140
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139576B2

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