Water → HCID 86681009, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(methylthio)benzo[d]thiazole-6-carbonitrile (10.0 g, 48.5 mmol) from Step 3 of this Example in THF (150 mL) was added lithium aluminum hydride solution (2.0 M in THF, 50.9 mL, 101.9 mmol) slowly at −78° C. The reaction mixture was slowly warmed to 0° C. and stirred at 0° C. for 3 h treated with 4 mL of water, 4 mL of 10% aq NaOH and 12 mL of water. The resulting reaction mixture was stirred at rt for 1 h before it was filtered through a Celite pad and the precipitates were washed with 100 of mL EtOAc. The combined filtrates were concentrated under reduced pressure. The crude product was purified on a silica gel column using a mixture of MeOH—CH2Cl2 (1:2, v/v) as eluent to give (2-(methylthio)benzo[d]thiazol-6-yl)methanamine as an yellow oil (3.5 g, 34%). 1H NMR (300 MHz, CDCl3) δ 7.82 (d, J=8.3 Hz, 1H), 7.73 (s, 1H), 7.35 (dd, J=1.4, 8.4 Hz, 1H), 3.97 (s, 2H), 2.79 (s, 3H), 1.55 (s, 2H). LCMS (ESI) m/z 211 (M+H)+.

Provenance & Evidence