Potassium Iodide → HCID 54052585, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-hydroxy-2-nitrobenzaldehyde (1.00 g, 6 mmol), 2-bromoethyl ethyl ether (1.00 g, 0.74 mL, 6.5 mmol), powdered potassium carbonate (0.91 g, 6.5 mmol), potassium iodide (catalytic quantity) and dimethylformamide (10 mL) was heated with stirring at 110° C. After 30 minutes, the mixture was cooled, diluted with water and extracted with dichloromethane (3 times). Combined extracts were washed with water (2 times), dried over sodium thiosulfate and concentrated in vacuo to leave an oil which was dissolved in ethanol (3 mL) and added to a stirred solution of sodium ethoxide (0.53 g, 78 mmol) and diethyl 2,4-dioxoimidazolidine-5-phosphonate (1.83 g, 77 mmol) in ethanol (15 mL). After 10 minutes, the mixture was diluted with 2N hydrochloric acid solution and the solid filtered off and dried in air to give 5-[[5-(2-ethoxyethoxy)-2-nitrophenyl]methylene]-2,4-imidazolidinedione as a partial hydrate (1.40 g, 73%), m.p. 228°-233° C. (dec.).

Provenance & Evidence