Benzocaine → HCID 22596839, compound

Participants

Reaction Steps

A solution of hexyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (17) (635 mg, 2.21 mmole) in 10 mL toluene was treated with 1.0 mL of a 20% phosgene solution in toluene, stirred at room temperature for nine hours and then concentrated in vacuo. The residue was diluted with 15 mL of pyridine and treated with 730 mg of ethyl p-aminobenzoate (2 eq.). The reaction mixture was heated to 40° C. for 15 hours and concentrated in vacuo to provide a orange oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes, dry pack) to provide 296 mg (28%) of ethyl 4-[3-hexyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (19) as a yellow oil.

Provenance & Evidence