1,1-Dichloroacetone → HCID 69428593, compound

Participants

Reaction Steps

MS: M=178.2 (API+). 1H-NMR(400 MHz, D6-DMSO): δ=3.79(s, 1H, OCH3), 6.46(d, 1H, 2-H), 6.97(d, 2H, 3′-/5′-H), 6.99(br, 1H, NH), 7.36(d, 1H, 3-H), 7.44(br, 1H, NH), 7.50(d, 2H, 2′-/6′-H). 48.0 g (271 mmol) 3-(4-Methoxyphenyl)-acrylamide, 44.4 g (350 mmol) dichloro acetone and 400 ml toluene were kept at reflux temperature for 24 h with continuous removal of water by applying a Dean-Stark trap. After removal of solvents in vacuo, the residue was intensively shaken with 600 ml water, the precipitate isolated by filtration, washed with water and heptane. Drying at 40° C. in vacuo gave 56.9 g (84%) 4-Chloromethyl-2-[2-(4-methoxyphenyl)-vinyl]-oxazole.

Provenance & Evidence