Dimethylformamide → HCID 53673532, compound

Participants

Reaction Conditions

Reaction Steps

The reaction mixture of 1-bromohexane (1.046 g, 0.00635 mol), sodium methanethiosulfonate (0.850 g, 0.00635 mol) and dry DMF (6 mL) was heated at 60° C. for 2 hr. At room temperature, water (15 mL) was added and the resulting mixture was extracted with ether (3×30 mL). The extracts were washed with brine, dried, concentrated and the residue was subjected to flash column chromatography on silica gel with EtOAc-hexanes (1:4) to afford a colorless liquid (2.057 g, 82%). IR (CDCl3 cast): 3030 (w), 3010 (w), 2955 (st), 2930 (st), 2860 (st), 1460 (m), 1320 (st), 1133 (st), 955 (st), 747 cm−1 (st); 1H NMR (200 MHz, CDCl3): δ 3.33 (s, 3H, CH3SO2S), 3.18 (t, J=7.4 Hz, 2H, SCH2CH2), 1.77 (pseudo p, J=7.2 Hz, 2H, SCH2CH2), 1.50-1.20 (m, 6H, CH2CH2CH2CH3), 0.90 (m, 3H, CH2CH3); 13C NMR (50 MHz, CDCl3): δ 50.64, 36.50, 31.13, 29.46, 28.26, 22.44, 13.96.

Provenance & Evidence