Hydrochloric Acid → HCID 67083770, compound

Participants

Reaction Steps

To a mixture of 2-((4-bromo-3-methoxyphenyl)diazenyl)-2-cyanoacetamide (Method 12) (34.4 g, 115.8 mmol) in toluene (250 ml) under N2 was added TiCl4 (51.1 ml, 463 mmol). The reaction mixture was stirred at reflux for 4 hours before being allowed to cool to room temperature. The reaction mixture was carefully poured over an ice cold solution of 3N HCl (˜600 ml), the mixture was then allowed to warm to rt, and was then stirred at 90° C. for 10 minutes. A precipitate formed which was collected via vacuum filtration, washed with water (˜200 mL), ethanol (˜200 mL), ether (˜200 mL), and dried in vacuo to yield the title compound as a brown solid which was used without further purification (30.0 g, 87%). 1H NMR: 10.30 (s, br, 1H), 9.95 (s, br, 1H), 9.15 (s, 1H), 8.55 (s, 1H), 8.09 (s, 1H), 7.68 (s, 1H), 4.15 (s, 3H); m/z 298.

Provenance & Evidence