Potassium Hydroxide → HCID 21997643, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-amino-6-fluoro-benzothiazole (5.13 g) was stirred for 6½ h at 165-170 ° C. under nitrogen in a solution of potassium hydroxide (10.3 g) in water (20 ml). The resulting mixture was cooled to 10° C. and adjusted to pH ˜8 by adding acetic acid, keeping the temperature below 25° C. The mixture was cooled to 10° C. and ethanol (30 ml) and iodoacetonitrile (2.20 ml) were added. After stirring for 15 min acetic acid (1.8 ml) was added and approx. half of the solvent was removed in vacuo. The residue was diluted with water (150 ml) and extracted with ethyl acetate (50 ml). The extract was dried over sodium sulfate, filtered and evaporated to give the title compound as a practically pure yellow oil. Yield 4.88 g (88%); 1H-NMR (DMSO-d6), δ (ppm): 7.26-7.14 (m, 1H, Ar—H), 7.09-6.95 (m, 1H, Ar—H), 6.85-6.72 (m, 1H, Ar—H), 5.36 (br, 2H, NH2), 3.99 (s, 2CH2).

Provenance & Evidence