Acetic Acid → HCID 21997633, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-amino-5-fluoro-benzothiazole (3.45 g) was stirred for 7 h at 165-170 ° C. under nitrogen in a solution of potassium hydroxide (6.9 g) in water (13.5 ml). The resulting mixture was cooled on an ice bath to 10° C., supplemented with water (5 ml) and then a solution of acetic acid (3.5 ml) in water (4 ml). The mixture was diluted with 96% ethanol (20 ml) and subsequently a solution of iodoacetonitrile (3.42 g) in 96% ethanol (5 ml) was added. After stirring for 15 min the mixture was adjusted to pH ˜7 by adding acetic acid and approx. half of the solvent was removed in vacuo. The residue was diluted with water (100 ml) and extracted with ethyl acetate (50+3×25 ml). The combined extracts were dried over sodium sulfate, filtered and evaporated to give the title compound as a practically pure yellow oil. Yield 3.60 g (96%); 1H-NMR (DMSO-d6), δ (ppm): 7.32-7.43 (dd, 1H, Ar—H), 6.49-6.60 (dd, 1H, Ar—H), 6.29-6.43 (ddd, 1H, Ar—H), 5.88 (br, 2H, NH2), 3.82 (s, 2H, CH2).

Provenance & Evidence