N-[1-(1-benzothiophen-2-yl)ethyl]hydroxylamine → HCID 10516789, compound

Participants

Reaction Steps

To a stirred solution of urea (7.27 g, 119 mmol) was added phenyl chloroformate (8.9 g, 57 mmol) followed by pyridine (30 mL). The resulting mixture became highly exothermic and soon solidified. This solid residue was dispersed and washed well with pyridine and ethylacetate to afford the intermediate N-phenoxycarbamoyl urea. A solution of N-(1-benzo[b]thien-2-yl)ethylhydroxylamine (0.50 g, 2.6 mmol) and N-phenoxycarbamoyl urea (0.46 g, 2.6 mmol) in dioxane (12 mL) was heated at 50° C. for 18 h. The mixture was then brought to 75° C. for 24 h. The reaction was cooled to r.t. and concentrated in vacuo. The resulting residue was crystallized in ethanol:hexanes to afford the desired product. (R1 =NHCONH2, A=CHCH3, X=S [2-isomer], Y=H, M=H).

Provenance & Evidence