Water → HCID 117806247, compound

Participants

Reaction Steps

To a solution of 2-nitrobenzenesulfonamide (XXX) (1 g, 4.95 mmol) in acetonitrile (1.5 mL) was added cesium carbonate (3.56 g, 10.93 mmol) followed by (R)-(−)-epichlorohydrin (XXXI) (1.6 mL, 20.4 mmol). This reaction mixture was refluxed for 16 hours. 100 mL of water was added to the cooled solution followed by extraction with EtOAc (3×75 mL) The organic layer was dried over sodium sulfate, the solvent removed under vacuum and the residue purified by automated silica gel chromatography using hexanes/EtOAc 0→100% to give 2-nitro-N,N-bis((R)-oxiran-2-ylmethyl)benzenesulfonamide (XXXII) (0.48 g, 1.5 mmol, 32% yield). 1H NMR (DMSO-d6) δ ppm 8.08 (d, J=7.8, 1H), 8.00 (d, J=7.8, 1H), 7.91 (t, J=7.6, 1H), 7.84 (t, J=7.6, 1H), 3.64 (ABq, J=4.0, 15.4, 2H), 3.38 (dd, J=3.6, 6.2, 2H), 3.12-3.08 (m, 2H), 2.75 (t, J=4.3, 2H), 2.59 (dd, J=2.6, 4.9, 2H), 2.50 (p, J=1.72, 2H). ESIMS found for C12H14N2O6S m/z 314.9 (M+H).

Provenance & Evidence