4-(Isocyanatomethyl)-1,2-dimethoxybenzene → HCID 44128380, Verbindung

HRID 2098292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098292
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:6][N:7]=[C:8]=[O:9].[N+:15](=[C:17]1[N:21]=[CH:20][N:19]=[C:18]1[C:22]([NH2:24])=[O:23])=[N-:16]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:6][N:7]1[C:8](=[O:9])[N:21]2[CH:20]=[N:19][C:18]([C:22]([NH2:24])=[O:23])=[C:17]2[N:15]=[N:16]1

Komponenten

4

Edukt 2

HCID 242713714-(Isocyanatomethyl)-1,2-dimethoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Produkt 1

HCID 44128380HCID 44128380, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Crude 3,4-dimethoxybenzyl isocyanate (4 mmol) was added to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry dimethylsulfoxide (2.5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the addition of ice and the solid product was removed by filtration and purified by column chromatography to give the title compound as a white solid. Yield: 0.068 g, 10%. IR vmax/cm−1 1734, 1686, 1616. 1H NMR δH (DMSO-d6) 3.73 (3H, s, OMe), 3.74 (3H, s, OMe), 5.42 (2H, s, CH2Ar), 6.91-6.98 (2H, m, ArH), 7.03 (1H, d, J=1.9, ArH), 7.70 (1H, br s, NH), 7.82 (1H, br s, NH), 8.83 (1H, s, 6-H). δC (DMSO-d6) 52.2, 56.0, 56.0, 112.1, 112.4, 121.1, 128.3, 129.4, 131.3, 134.9, 139.6, 149.1, 149.2, 162.0.

Aufarbeitung

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product was removed by filtration
  3. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-094db4d20e9d45c8abab26aafc101605
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450479B2

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