Triethylamine → HCID 67363188, compound

Participants

Reaction Steps

To a solution of 11 (47 mg, 0.18 mmol) in dry methylene chloride (10 mL), under argon, were added SOCl2 (15 μl, 0.21 mmol) and triethylamine (29 μl, 0.21 mmol). The solution was stirred at room temperature for 45 min then the solvent was removed in vacuo. The crude product was purified by chromatography using CH2Cl2/EtOH (97/3, v/v) as eluent to give compound 12 (26 mg, 52%); mp 270-272° C.; IR (KBr) 1701, 1248, 1189 cm−1; 1H NMR (400 MHz, (acetone-d6) δ 1.41 (t, 3H, J=7 Hz), 4.41 (q, 2H, J=7 Hz), 4.86 (s, 2H), 7.20 (d, 1H, J=7 Hz), 7.52 (s, 1H), 7.90 (s, 1H), 8.28 (d, 1H, J=7 Hz), 11.63 (brs, 1H); 13C NMR (100 MHz, (acetone-d6) δ 14.7, 40.6, 61.3, 102.9, 107.9, 113.1, 114.7, 125.0, 127.5, 134.3, 140.9, 142.3, 161.5; MS m/z 279 (M++2, 9), 277 (M+, 20), 196 (43), 149 (33), 85 (63), 71 (72), 57 (100). Anal. Calcd for C13H12ClN3O2: C, 56.22; H, 4.36; N, 15.13. Found: C, 56.07; H, 4.43; N, 15.10.

Provenance & Evidence