Water → HCID 72334043, compound

Participants

Reaction Steps

A mixture of 3-[(5-chloro-1,3-benzothiazol-2-yl)methoxy]-2,6-difluoro-N′-hydroxybenzenecarboximidamide (222, mg, 0.6 mmol, 1 equiv.), 0.7 N NaOH solution (0.97 ml, 0.68 mmol, 1.13 equiv.) and dimethylsulfate (0.60 ml, 0.63 mmol, 1.05 equiv.) in THF (4 ml) was stirred at 0° C. for 6 h. The mixture was poured into H2O (40 ml) and the precipitant solid was filtered and washed with H2O (2×10 ml) and Et2O (2×10 ml) to give 43 mg (yield 19%) of the desired product. Purity 70% by HPLC (Gemini C18, 50×4.6 mm): m/z 384 [M+H]+, Rt=3.26 min. HPLC-MS analysis suggested also that there was 23% un-reacted starting material and 6% of the N-methylated by-product: 3-[(5-chloro-1,3-benzothiazol-2-yl)methoxy]-2,6-difluoro-N′-hydroxy-N-methylbenzenecarboximidamide.

Provenance & Evidence