Benzocaine → HCID 11784539, compound

Participants

Reaction Conditions

Reaction Steps

A solution of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride (35) (900 mg, 2.6 mmole) in 20 mL pyridine was treated with 481 mg of ethyl p-aminobenzoate (3 eq.) and stirred at 40° C. for 15 hours. The reaction mixture was diluted with 100 mL of cold water and extracted with two 100 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give an orange oil, which was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes) to provide 260 mg of ethyl 4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (37) as a pale yellow oil.

Provenance & Evidence