[C:1]1([S:11]([NH2:14])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CC(=O)CC.O.CCOC(C)=O>[C:1]1([S:11]([NH:14][C:22](=[O:23])[O:24][CH2:25][CH3:26])(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1
A mixture of 1-naphthalene sulfonamide (769 mg, 3.67 mmol) and potassium carbonate (563 mg, 4.07 mmol) in 2-butanone (9 ml) was heated under reflux for 30 min. Ethyl chloroformate (430 mg, 3.96 mmol) was added dropwise and the resulting solution was heated under reflux for 3 h. The mixture was cooled and diluted with H2O (30 ml) and AcOEt (10 ml). The aqueous layer was collected and adjusted to pH 2 by addition of 1N HCl (aq). Extraction with AcOEt (2×20 ml) and concentration of the dried organic extracts afforded ethyl 1-naphthylsulfonylcarbamate (674 mg, 67%) as a white solid. 1H NMR (DMSO-d6): δ 12.35 (bs, 1H), 8.57 (1H, d, J 8.6), 8.29 (2H, m), 8.11 (1H, d, J 7.7), 7.71 (3H, m), 3.90 (2H, q, J 7.1), 0.99 (3H, t, J 7.1).
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