Hydrochloric Acid → HCID 68485825, compound

Participants

Reaction Conditions

Reaction Steps

Concentrated HCl (4 ml) is added slowly to a solution of N-[2-hydroxymethyl-4-(trifluoromethoxy)phenyl]-pivaloylamide (0.35 g, 1.2 mmol) in dioxane (3 ml) and the resulting reaction mixture heated at 80° C. for 4 hours, then diluted with isopropanol (20 ml), and thiourea (0.14 g, 1.8 mmol) added and the mixture refluxed for 20 hours. The solvent is then evaporated under vacuum and the residue diluted with H2O, basified with 2 N NaOH, and extracted with CH2Cl2. The combined organic extracts are dried over Na2SO4 and concentrated under vacuum. The residue is purified by chromatography through silica, eluting with AcOEt/petroleum ether (1:1). The product is obtained as a yellow solid, with a yield of 84%. Recrystallisation from EtOH gives a solid with m.p. 115-118° C. 1H-NMR (CDCl3): 3.87 (s, 2H), 5.16 (br s, 2H), 6.97-7.11 (m, 3H). MS (ESI): m/z 249 (M+H+).

Provenance & Evidence