1-Bromo-2-Chloroethane → HCID 28917003, compound

Participants

Reaction Steps

To a cold (0° C.) suspension of sodium hydride (823 mg, 60% in oil, 0.0206 mol) in N,N-dimethylformamide (20 mL) was added a solution of tetrahydro-2H-1,2-thiazine 1,1-dioxide (2.53 g, 0.0187 mol) in N,N-dimethylformamide (30 mL). The resulting mixture was stirred at room temperature 1 hour. 1-Bromo-2-chloroethane was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, then chromatographed on silica gel (30 to 70%, ethyl acetate in hexanes). The resulting residue was triturated with ether and the solids were filtered off. The filtrate was concentrated to give 2-(2-chloroethyl)tetrahydro-2H-1,2-thiazine 1,1-dioxide, which was partially contaminated with starting material, and was taken on to the next step. 1H NMR (400 MHz, CDCl3) δ 3.60 (t, J=6.6 Hz, 2 H), 3.47-3.42 (m, 4 H), 3.01 (t, J=6.0 Hz, 2 H), 2.18 (m, 2 H), 1.66 (m, 2 H).

Provenance & Evidence