Dimethylformamide → 6-Chloro-5-formyl-1,3-dimethyluracil

Participants

Reaction Steps

Phosphorous oxychloride (690 ml) was added slowly to dry N,N-dimethyl formamide (180 ml) at 0° C. The mixture was then allowed to warm to room temperature. 1,3-Dimethylbarbituric acid (60 g, 384.27 mmol) was added portion wise and refluxed for 45 min. The excess of phosphorous oxychloride and DMF were distilled off under reduced pressure and the viscous residue was poured into ice-cold water (2000 ml). The reaction mixture was allowed to room temperature and extracted with chloroform (3×500 ml). The combined organic extracts were dried over Na2SO4 and concentrated. The crude material obtained was then stirred in 10% ethyl acetate in hexane (150 ml) to obtain 58 g of the product as the pale yellow solid; 1H NMR (300 MHz, CDCl3) δ 3.41 (s, 3H), 3.69 (s, 3H), 10.18 (br s, 1H).

Provenance & Evidence