Acetic Acid → 6-Ethylamino-2-benzothiazolesulfonamide

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (378 mg, 0.01 mole) and 6-amino-2-benzothiazolesulfonamide (459 mg, 0.002 mole) are ground together, then added very slowly over 1 hr. to glacial acetic acid (5 ml.) with stirring under nitrogen at 20° C. After the vigorous evolution of hydrogen has subsided, the reaction mixture is stirred at 20° C. for 3 hrs, treated with H2O, filtered, and made basic with 10N NaOH solution. Neutralization with aqueous HCl followed by extraction with EtOAc and concentration to dryness gives 6-ethylamino-2-benzothiazolesulfonamide. ##STR11## NMR (d6 -DMSO) δ1.21 (3H, t, CH3CH2 --), 3.11 (2H, q, CH3CH2), 3.44 (1H, br s, NH), 6.94 (1H, dd, J=9 Hz, J=3 Hz, Hb), 7.11 (1H, d, J=3 Hz, Hc), 7.79 (1H, d, J=9 Hz), Ha), 8.07 (2H, br s, SO2NH2).

Provenance & Evidence