Propargyl bromide → Methyl Isocyanate

HRID 466751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466751
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]([CH2:7][C:8]#[CH:9])[C:3]1=[O:10].C(OC(OCC)CN)C.C(Br)C#C>>[CH2:7]([N:4]1[CH:5]=[CH:6][NH:2][C:3]1=[O:10])[C:8]#[CH:9].[CH3:1][N:2]=[C:3]=[O:10]

Komponenten

5

Edukt 3

HCID 7842Propargyl bromideHCID 695242,2-DiethoxyethylamineHCID 150655051,3-Dihydro-1-methyl-3-(2-propyn-1-yl)-2H-imidazol-2-one

Produkt 2

HCID 12228Methyl IsocyanateHCID 197532861,3-dihydro-1-(2-propynyl)-2H-imidazol-2-one

Versuchsvorschrift

The 1,3-dihydro-1-(2-propynyl)-2H-imidazol-2-one intermediates were prepared as outlined in Scheme 2 for the synthesis of 1,3-dihydro-1-methyl-3-(2-propynyl)-2H-imidazol-2-one (X). Aminoacetaldehyde diethyl acetal was reacted with propargylbromide to give a mixture of the tertiary and secondary amines VII and VIII which were separated by chromatography on silica gel. Treatment of VIII with methyl isocyanate gave IX and this was heated in aqueous oxalic acid to give 1-methyl-3-(2-propynyl)-2H-imidazol-2-one (X).

Aufarbeitung

  1. customto give
  2. customwere separated by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-086015f787cf4bb298d0ead5fb4c3436
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157124

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