Iodoethane → HCID 10224080, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-[3-ethyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (0.25 g, 0.6 mmole) in 15 mL DMF was treated portionwise with 22 mg of sodium hydride (0.92 mmole). After 5 minutes, ethyl iodide (0.062 mL) was added and the reaction mixture was heated to 150° C. for three days. The solvent was removed in vacuo and the residue was diluted in 25 mL ethyl acetate. The organic phase was washed with two 10 mL portions of water and one 10 mL portion of HCl 1N. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 10% methanol/methylene chloride) giving 90 mg of 4-[1,3-diethyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid as a pale brown solid. M.P. 169-172° C.

Provenance & Evidence