Dimethyl Sulfate → HCID 10589184, compound

Participants

Reaction Steps

To a suspension of sodium hydride (4.80 g, 0.2 mol, 2 eq, 60% dispersion in mineral oil) in tetrahydrofuran (100 mL) was slowly added malonodinitrile (6.61 g, 0.1 mol). 4-Nitrobenzoyl chloride (18.8 g, 0.1 mol, 1 eq) was then added in portions while keeping the reaction temperature below 10° C. The reaction mixture was stirred for 1 hour at room temperature. Dimethyl sulfate (15.1 g, 0.12 mol, 1.2 eq) was then added and the reaction mixture was refluxed for 2 hours. Triethylamine (25.3 g, 0.25 mol, 2.5 eq), followed by tert-butyl hydrazine hydrochloride (12.4 g, 10 mmol), was added and the reaction mixture was heated under reflux for an additional hour. The solvent was then evaporated and 50 mL of ethanol were added. The reaction mixture was heated under reflux, and water (250 mL) was added while keeping the temperature above 50° C. The reaction mixture was then cooled to 10° C. and 5-amino-1-tert-butyl-3-(4-nitro-phenyl)-1H-pyrazole-4-carbonitrile was isolated by filtration. 1H-NMR (DMSO-d6): ppm 1.59 (s, 9H), 6.55 (br s, 2H), 8.05 (d, 2H, J=7.2 Hz), 8.33 (d, 2H, J=7.2 Hz). LC MS (m/e)=285.8 (MH+).

Provenance & Evidence