Hydrochloric Acid → [2-(5-Phenyl-thiazol-2-ylamino)-pyridin-6-yl]-methanol

Participants

Reaction Steps

(6-Hydroxymethyl-pyridin-2-yl)-thiourea (6-3) 1.05 g (5.73 mmol) and (1-bromo-2,2-dimethoxy-ethyl)-benzene (2.11 g, 8.60 mmol) were stirred in 18 mL EtOH. Concentrated HCl (aq), 6 mL, was added and the mixture was heated to reflux. After 7 h, additional (1-bromo-2,2-dimethoxy-ethyl)-benzene (1.05 g, 4.30 mmol) and conc HCl (aq), 3 mL were added. The reaction was then heated at reflux for an additional 14.5 h. The reaction was poured into 120 mL water and the pH was adjusted to 7 with Na2CO3 (s). A precipitate formed which was filtered and washed with water. The solid was triurated with 50 mL ether, filtered and washed with ether to provide the titled compound as a white solid. 1H NMR(CD3OD): δ7.72 (t, 1H, J=7.7 Hz), 7.58 (s overlapping with d, 3H), 7.38 (t, 2H, 7.5 Hz), 7.25 (t, 1H, J=7.3 Hz), 7.07 (d, 1H, J=7.5 Hz), 6.90 (d, 1H, J=8.3 Hz), 4.76 (s, 2H). Mp: 196-198° C. M+1: 284.0.

Provenance & Evidence