Citric Acid → HCID 14227207, compound

Participants

Reaction Steps

To a solution of this urea (1.59 g, 8.19 mmol) in DMF (13 ml) at 50° C. under nitrogen was added sodium hydride (360 mg of a 60% dispersion in oil). The resulting solution was stirred for 45 minutes, and 1-bromooctane (1.83 ml) was added. After 16 hours, the mixture was poured into 1% aqueous citric acid (75 ml) and extracted 3 times with 1:1 hexane-ether. The combined extracts were dried (MgSO4), filtered, and evaporated. Purification by chromatography on silica provided N-benzyloxy-N-octyl-N',N'-dimethylurea as a colorless oil (2.04 g, 81% yield). Hydrogenolysis as in Example 2 above, and recrystallization from hexane at -40° C., provided the title compound as a white solid (875 mg, 57% yield), mp 29°-30° C.

Provenance & Evidence