Phosgene → HCID 22600036, compound

Participants

Reaction Steps

A solution of (2-ethoxy-ethyl)-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (37) (484 mg, 1.76 mmole) in 5 mL toluene was treated with 0.96 mL of a 20% phosgene solution in toluene, stirred at room temperature for 12 hours and then concentrated in vacuo. The residue was diluted with 7.2 mL of pyridine and treated with 530 mg of methyl p-aminobenzoate (2 eq.), heated at 40° C. for 15 hours, then concentrated in vacuo to give an orange oil. The product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes, dry pack) to provide 520 mg (44%) of methyl 4-[3-(2-ethoxy-ethyl)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (39) as a colorless oil.

Provenance & Evidence