Dimethyl-p-toluidine → [3-(3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-8-methoxy-4H-2,5,10b-triaza-benzo[e]azulen-6-yl]-hydrazine

Participants

Reaction Steps

3-(3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-8-methoxy-4,5-dihydro-2,5,10b-triaza-benzo[e]azulen-6-one (1 g, 3 mmol) and N,N-dimethyl-p-toluidine (0.856 mL, 5.9 mmol) were mixed in toluene (25 mL), treated with phosphoryl bromide (0.935 g, 3.3 mmol), and refluxed for 15 h. Toluene was evaporated and the residue extracted with CH2Cl2 (50 mL) and water (50 mL). The organic layer was dried, evaporated, redissolved in THF (50 mL), and treated with a 1 M solution of anhydrous hydrazine in TBF (10 mL, 10 mmol) at reflux overnight. The mixture was evaporated and directly chromatographed on silica gel in CH2Cl2/MeOH 10:1. One obtained a light brow solid (0.4 g, 38%). m/z 352 (MH+).

Provenance & Evidence