Sodium hydride → HCID 66746957, Verbindung

To a solution of 3-hydroxy-2,2-dimethyl-N-propylpropanamide (1.59 g, 10.0 mmol) (Example 197d) in dry THF (30 mL) was carefully added NaH (60% in mineral oil, 400 mg, 10.0 mmol) in small portions at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. under nitrogen for 2 hrs. To this solution was added 2,6-dinitrobenzonitrile (1.93, 10.0 mmol), and the reaction solution was stirred at 0° C.—RT under nitrogen overnight. The reaction mixture was quenched with brine, and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting with 60% EtOAc in hexanes to give the title compound as a pale yellow solid (2.21 g, 72%). MS 306 (MH+).

1. customat 0° C.
2. stirringthe reaction solution was stirred at 0° C.—RT under nitrogen overnight
3. customThe reaction mixture was quenched with brine
4. extractionextracted with EtOAc (3×)
5. washThe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. customAfter evaporation of the solvent
8. customthe residue was purified by chromatography on silica gel eluting with 60% EtOAc in hexanes

ORD-Eintrag

ord-bb285b0c0929407ebe3863cdcd02f718

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09000054B2