Methylamine → HCID 25104409, compound

Participants

Reaction Conditions

Reaction Steps

Tetrahydro-2H-thiopyran-4-one (1.0 g, 8.6 mmol) was dissolved in methanol (40 ml), and methylamine in ethanol (3.3 ml of a 33% solution) was added and the mixture stirred at room to temperature for 1 h. The mixture was cooled to −78° C. and a suspension of LiBH4 (0.34 g) in THF (10 ml) was added and stirred for 18 h whilst warming up to room temperature. Water (1 ml) was added and then evaporated and the residue dissolved in chloroform (20 ml). Triethylamine (2 ml) was added and the mixture cooled to 0° C. before adding slowly a solution of [2,1,3]-benzoxadiazole-5-carbonylchloride (1.28 g, 7 mmol) in chloroform (15 is ml). The mixture was stirred for 0.5 h and then washed with water (100 ml) and HCl (→pH 2) and NaHCO3 solution (100 ml). The aqueous was extracted with chloroform (100 ml) and the combined organics were dried (MgSO4) and concentrated under vacuum to give a white solid after trituration with diethyl ether (1.6 g). Mp=155-156° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.92 (d, J=9.3 Hz, 1H); 7.83 (sb, 1H); 7.40 (d, J=9.3 Hz, 1H); 4.60-4.45 and 3.50-3.30 (m, 1H); 3.10-2.40 (m, 7H) and 2.20-1.85 ppm (s, 4H).

Provenance & Evidence