Isoamyl Nitrite → HCID 13714613, compound

Participants

Reaction Conditions

Reaction Steps

Add isopentyl nitrite (0.5 mL, 3.75 mmol) to a stirred 5° C. solution of ethyl 1-methyl-5-amino-1H-pyrazole-4-carboxylate (1.69 g, 10.0 mmol) and dimethyl disulfide (1.79 mL, 20.0 mmol) in CHCl3 under nitrogen in a 3-necked flask equipped with a thermometer and a condenser. Allow the reaction to warm to 20° C. in a H2O bath, and treat with additional isopentyl nitrite (1.5 mL, 11.3 mmol) dropwise. After 15 min, remove the reaction from the 20° C. H2O bath (exotherm raises temperature to 50° C. over approximately 1 min). Stir at ambient temperature under N2 overnight. Wash with H2O, and separate the layers. Extract the aqueous layer with CHCl3, combine the organic layers, dry over MgSO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (gradient of 0 to 35% EtOAc in hexanes) to afford the title compound (1.94 g, 97%). ES/MS m/z 201.0 (M+1).

Provenance & Evidence