1,2-Dichloroethane → 2-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]-N-propylacetamide

Participants

Reaction Steps

To a stirred solution of 24 (110.3 mg, 0.41 mmol) and n-propylamine (50.5 mg, 0.50 mmol) in CHCl3 (2.0 ml), HOBt (190 mg, 1.41 mmol) and EDC (120 mg, 0.63 mmol) were added at room temperature. After stirring for 20 hours, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 solution and brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by HPLC (gradient from 20%, acetonitrile 80% in DDW to 100% acetonitrile, in 15 minutes) to give 33 (57.9 mg, 36% yield) as a brown amorphous solid, range of m.p. temperature was too large for a clear determination. 1H NMR (DMSO-d6): δ 0.97 (t, 3H, J=6.8), δ 1.27 (t, 3H, J=7.1), δ 1.53 (m, 2H, J=6.8, 3.5), δ 3.54 (d, 2H, J=3.7), δ 4.01 (s, 2H), δ 4.19 (q, 2H, J=7.3), δ 6.23 (amide broad peak), δ 6.97 (dd, 1H, J=10.8, J=3.7), 7.33 (d, 2H, J=8.8). 13C NMR (DMSO-d6): δ 12.8, 13.76, 20.6, 39.56, 40.78, 65.1, 101.79, 114.78, 123.6, 135.79, 145.8, 154.67, 168.4, 169.95. MS: MW=310.07 g/mol, MNa+=333.18 g/mol.

Provenance & Evidence