O-Phenylenediamine → HCID 1486498, compound

Participants

Reaction Steps

A 100 mL flask fitted with a stir-bar and condenser was charged with 1,2-phenylenediamine (2.88 g, 26.6 mmol), (phenylthio)acetic acid (4.00 g, 26.6 mmol), and 4M HCl (40 mL). The resultant suspension was heated in a 130° C. bath 48 hr. The mixture was cooled and concentrated in vacuo to a brown syrup. The syrup was taken up in EtOAc (100 mL) and washed with saturated NaHCO3 (2×75 mL) and brine (50 mL). The solution was filtered through phase separation paper and concentrated in vacuo to a tan solid. The crude solid was triturated with hexanes:EtOAc 6:1 (50 mL), filtered, pressed with rubber dam, and rinsed with hexanes:EtOAc 4:1 (2×10 mL). The material was dried to give 4.4 g of 68 as a tan solid (77%). 1H NMR (300 MHz, CDCl3): δ 11.7 (bs, 1H), 7.7-7.4 (m, 2H), 7.4-6.9 (m, 7H), 4.4 (s, 2H) ppm. HPLC analysis (15:10:75 H2O:A1:MeOH) showed a purity of 99% with retention time of 4.0 min.

Provenance & Evidence