Ethylamine → N-ethyl-3-chloro propylsulfonamide

Participants

Reaction Steps

To a solution of 3-chloropropylsulfonyl chloride (1) (6.1 g, 34.5 mmol) in ether (25 ml) was dropwise added ethylamine (2a) (a 70% aqueous solution, 4.4 g, 68.3 mmol) with stirring and ice-cooling over 15 minutes, and the resultant mixture was stirred for one hour at room temperature. The reaction mixture was concentrated in vacuo, Benzene (100 ml) was added to the residue, and the solvent was removed in vacuo. To the residue was added ether (150 ml) and filtered to remove the insoluble material. The filtrate was distilled in vacuo to remove ether and 6.96 g (yield, about 100%) of crude N-ethyl-3-chloro propylsulfonamide (intermediate 3a) was obtained as colorless crystals (m.p.=30-32° C.). To a solution of this intermediate (3a) (6.96 g, 34.5 mmol) in THF (50 ml) was slowly added sodium hydride (60% in oil, 1.52 g, 38.0 mmol) with stirring under ice-cooling over 15 minutes. To reaction mixture was stirred for another 30 minutes at room temperature. After the addition of the ether (50 ml), the mixture was filtered to remove insoluble material and solvent was distilled in vacuo to gi 4.93 g (96%) of the desired compound 4a as a pale yellow oil. IR (CH3Cl) cm−1: 3018, 2976, 2868, 1452, 1306, 1220, 1179, 1129, 1015; NMR (CDCl3)δ: 1.24 (3H, t, J=7.4 Hz), 2.28-2.42 (2H, m, CH2), 3.10 (2H, q, J=7.4 Hz, CH2), 3.15 (2H, t, J=7.6 Hz, CH2), 3.22-3.29 (2H, m, CH2).

Provenance & Evidence