Benzene → HCID 54083964, compound

Participants

Reaction Conditions

Reaction Steps

3-Methoxymethacrylic acid chloride (2.68 g) and 25 mL of benzene are combined in a round bottom flask. To this mixture is added 6.4 g of silver cyanate and the resultant mixture heated to reflux temperature. After 40 min at reflux temperature the mixture is cooled to -15° C. In a separate round bottom flask, 1.0 g of the product of Step A of Example 8, 30 mL of dimethyl formamide (DMF) and 10 mL of diethyl ether are combined and this second mixture cooled to -15° C. The acylisocyanate mixture is added to the amine and the resultant solution stirred at -15° C. for 2 h. and allowed to stand in the refrigerator overnight. The reaction mixture is concentrated and the crude material is purified by column chromatography. The material recovered from the column and 5 mL of 2N aqueous sulfuric acid solution are combined in a round bottom flask and this reaction mixture heated at reflux temperature for 2 h. The mixture is adjusted to pH 7 with aqueous barium hydroxide, filtered and the filtrate concentrated. The residue is purified by column chromatography to afford the title compound.

Provenance & Evidence