Diethyl Ether → HCID 44128897, Verbindung

HRID 2098308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098308
[CH2:1]([O:3][P:4]([CH2:9][N:10]=[C:11]=[O:12])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[N+:13](=[C:15]1[N:19]=[CH:18][N:17]=[C:16]1[C:20]([NH2:22])=[O:21])=[N-:14].CCOCC>CCOC(C)=O.CS(C)=O>[CH2:6]([O:5][P:4]([CH2:9][N:10]1[C:11](=[O:12])[N:19]2[CH:18]=[N:17][C:16]([C:20](=[O:21])[NH2:22])=[C:15]2[N:13]=[N:14]1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 15739370Diethyl (isocyanatomethyl)phosphonateHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Produkt 1

HCID 44128897HCID 44128897, VerbindungAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Isocyanatomethyl-phosphonic acid diethyl ester (953 mg, 6.95 mmol) in EtOAc (10 mL) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.5 g, 3.65 mmol) in dry dimethylsulfoxide (10 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature for 16 hours. The mixture was poured into Et2O and the resultant collected by filtration and washed with Et2O (3 reaction volumes) and dried to give the title compound as a solid (1.14 g, 50%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.91 (1H, s), 7.88 (1H, s), 7.74 (1H, s), 4.85 (2H, t, J=11.2 Hz), 4.12 (4H, m), 1.25 (6H, t, 7.2).

Aufarbeitung

  1. filtrationthe resultant collected by filtration
  2. washwashed with Et2O (3 reaction volumes)
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4935e962477b458d8fefc144d6e0e52b
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450479B2

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