Sodium hydride → HCID 66746957, compound

Temperature

0 °C

To a solution of 3-hydroxy-2,2-dimethyl-N-propylpropanamide (1.59 g, 10.0 mmol) (Example 215d) 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 record

ord-4100ff2ae17e4569858a180e7358c177

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633186B2