2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86675237, compound

Participants

Reaction Steps

Heat a mixture of 6-chloro-2-methyl-N4-(2-methylsulfanylethyl)pyrimidine-4,5-diamine (1.63 g, 0.007 mol), 2-chlorobenzaldehyde (1.96 g, 0.014 mol), and 15% FeCl3 on SiO2 (4.89 g) in 1,4-dioxane (15 mL) to 100° C. for 16 h. Cool the reaction and remove the silica by filtration through diatomaceous earth. Concentrate the filtrate under reduced pressure to give a residue. Dissolve the residue in dry dichloromethane (10 mL) and add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.58 g, 0.007 mol) at 0° C. Stir the reaction mixture at room temperature for 2 h. Dilute the reaction mixture with dichloromethane, and wash with 1 N aqueous sodium hydroxide solution, water and brine. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to give a residue. Purify the residue on a silica gel column eluting with ethyl acetate:hexane (15:85) to give the title compound (1.9 g). ES/MS m/z 353 (M+1).

Provenance & Evidence