[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].Cl[S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8].C(N(CC)CC)C.Cl.[Cl:21][CH2:22][CH2:23][CH2:24][NH2:25]>C(Cl)Cl>[Cl:21][CH2:22][CH2:23][CH2:24][NH:25][S:7]([NH:10][C:11](=[O:12])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:9])=[O:8]Tert-butyl alcohol (2.45 g, 33 mmol) was added to chlorosulfonyl isocyanate solution (4 g, 28.26 mmol) in CH2Cl2 (80 mL) at 0° C. and agitated for 30 min. Triethylamine (19.7 mL) and 3-chloropropylamine HCl (4.29 g, 33 mmol) were added to the mixture and agitated for 2 hr at room temperature, followed by extraction using CH2Cl2 and brine and drying over anhydrous MgSO4. The residue was purified by silica gel column chromatography to give tert-butyl N-(3-chloropropyl)sulfamoylcarbamate (2, 4.17 g, 54%). 1H NMR (300 MHz, CDCl3): δ 5.25 (br, 1H), 3.67-3.62 (m, 2H), 3.28-3.26 (m, 2H), 2.09-2.01 (m, 2H), 1.51 (S, 9H).
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