Phosgene → HCID 11484465, compound

Participants

Reaction Steps

A solution of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (51) (390 mg, 1.45 mmole) in 6 mL toluene was treated with 0.9 mL of a 20% phosgene solution in toluene and stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo to give pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride as a pale yellow solid. The solid was dissolved in 5 mL pyridine, treated with 0.5 g of methyl 4-amino-3-fluorobenzoate and stirred at 40° C. for three days. Volatile material was removed in vacuo and the residue subjected to flash chromatography (SiO2, 20% ethyl acetate/hexanes), yielding 17 mg of methyl 3-fluoro-4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate.

Provenance & Evidence