Sodium Thiosulfate → 1-Amino-N-phenyl-1H-imidazole-2-carboxamide
Reaktionsgleichung
[H-].[Na+].[C:3]1([NH:9][C:10]([C:12]2[NH:13][CH:14]=[CH:15][N:16]=2)=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)(=O)[NH2:24])C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[NH2:24][N:16]1[CH:15]=[CH:14][N:13]=[C:12]1[C:10]([NH:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:11]Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
0.430 g (10.75 mmol) of sodium hydride (60% dispersion in mineral oil) was added to a 0° C. cooled solution of N-phenyl-1H-imidazole-2-carboxamide (1.55 g, 8.27 mmol) in DMF (50 mL). The mixture was stirred at 0° C. for 30 minutes and 2.70 g (11.57 mmol) of DPPONH2 (P,P-diphenylphosphinic amide, available from Sigma Aldrich®, cat. no. 5994-87-6) were added portionwise. A thick suspension formed and additional 100 mL of DMF were added. The mixture was stirred at room temperature for 3 hours and then it was poured into 150 mL of a saturated aqueous solution of sodium thiosulphate and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated. The crude product was purified by flash chromatography (20% to 40% AcOEt/Hexanes) to yield 1.27 g (76% yield) of the title compound as a pale yellow solid.
Aufarbeitung
- addition5994-87-6) were added portionwise
- customA thick suspension formed
- stirringThe mixture was stirred at room temperature for 3 hours
- extractionextracted with ethyl acetate
- dry with materialThe combined organic layer was dried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by flash chromatography (20% to 40% AcOEt/Hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-d0cc1334dd974c8cafb4870783af19a5
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09340547B2
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