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0 °C

Sodium azide (13.12 g, 0.2018 mol) was suspended in CH3CN (200 mL) and the suspension cooled to 0° C. (ice bath). Sulfuryl chloride (27.24 g, 0.2018 mol) was added dropwise over 20 min. The ice bath was removed and stirring continued for 20 h at room temperature (a septum and balloon were mounted on the reaction flask). The reaction mixture was cooled to 0° C. (ice bath) and imidazole (26.11 g, 0.3835 mol) added over 20 min. After stirring for 3 h 15 min at room temperature the suspension was diluted with EtOAc (400 mL) and washed with H2O (2×400 mL) and saturated NaHCO3 solution (2×400 mL). The solution was dried with anhydrous MgSO4 and cooled to 0° C. (ice bath). Acetyl chloride (23.76 g, 0.3027 mol) was added dropwise to icecold EtOH (75 mL) over 10-15 min. After stirring for 10 min at 0° C. the solution was added to the EtOAc solution over 20 min. After stirring for 10 min the resulting suspension was filtered and the precipitate washed with EtOAc (4×100 mL) and dried under suction for 30 min affording the title compound as a white solid (31.81 g, 75%) with spectral characteristics in accordance with literature data7; 1H NMR (200 MHz, D2O) δ 9.43 (t, J=1.4 Hz, 1H), 8.05 (dd, J=2.1, 1.8 Hz, 1H), 7.64 (dd, J=2.1, 1.2 Hz, 1H); 13C NMR (75 MHz, D2O) δ 138.0, 123.1, 120.6; HRMS (m/z): M+ calcd. for C3H4N5O2S, 174.0085. found, 174.0085; Anal. Calcd. for C3H4ClN5O2S: C, 17.19; H, 1.92; N, 33.41. Found: C, 17.4; H, 2.1; N, 33.5.

1. customThe ice bath was removed
2. additionadded over 20 min
3. stirringAfter stirring for 3 h 15 min at room temperature the suspension
4. washwashed with H2O (2×400 mL) and saturated NaHCO3 solution (2×400 mL)
5. dry with materialThe solution was dried with anhydrous MgSO4
6. temperaturecooled to 0° C. (ice bath)
7. stirringAfter stirring for 10 min at 0° C. the solution
8. stirringAfter stirring for 10 min the resulting suspension
9. filtrationwas filtered
10. washthe precipitate washed with EtOAc (4×100 mL)
11. customdried under suction for 30 min