Pyridine → 1,1-Dimethylethyl N-(aminosulfonyl)carbamate

Temperature

0 °C

To chlorosulfonyl isocyanate (2.45 mL, 28 mmol) in toluene (38 mL) at −10° C. (ice/methanol bath) was added t-butyl alcohol (2.66 mL, 28 mmol) dropwise. The resulting solution was stirred at 0° C. (ice bath) for 20 min. Pyridine (5.0 mL, 62 mmol) was added dropwise with the ice/methanol bath at −15° C. to −10° C. The resulting mixture was stirred with ice bath at 0° C. for 40 min. Ammonium hydroxide (28%, 10 mL, 163 mmol) was then added dropwise with the ice/methanol bath at −10° C., followed by H2O (3 mL). The resulting mixture resulting was stirred with ice bath at 0° C. for 2.5 h. The resulting two layers were separated. The aqueous layer was washed with toluene (15 mL). The combined toluene layers were extracted with H2O (13 mL). The combined aqueous layers were acidified with 24% H2SO4 to pH 2. The resulting precipitate was filtered, washed with H2O (2×13 mL) and dried to yield the title compound as a white solid.

1. stirringThe resulting mixture was stirred with ice bath at 0° C. for 40 min
2. customThe resulting mixture resulting
3. stirringwas stirred with ice bath at 0° C. for 2.5 h
4. customThe resulting two layers were separated
5. washThe aqueous layer was washed with toluene (15 mL)
6. extractionThe combined toluene layers were extracted with H2O (13 mL)
7. filtrationThe resulting precipitate was filtered
8. washwashed with H2O (2×13 mL)
9. customdried

ORD record

ord-3b62872b2a1a44ecb935616549a6a8d7

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809554B2