Acetone → HCID 18976935, compound

Participants

Reaction Steps

Under nitrogen atmosphere, 191 g (2.61 mol) of dimethylformaldehyde and 100 ml of 1,2-dichloroethane were put in a 1 L three-hole flask provided with an agitator, a thermometer, and a reflux condenser, and after cooling the mixture sufficiently to the temperature of 0° C., 197.6 g (1.29 mol) of phosphorous oxychloride was dropped down slowly thereto. The temperature of the reactant was raised to room temperature, and then the reactant was agitated for 1 hour, recooled to 0° C. and 21.0 g (0.067 mol) of N-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}carbazole diluted with 30 ml of 1,2-dichloroethane was added slowly thereto. After 1 hour, the reaction temperature was raised to 90° C. and the reaction was carried out for 24 hours. After reaction, the temperature was dropped to room temperature, and the reactant was diluted with 1.5 L of ice water, and then was extracted three times with 200 ml of dichloromethane. The extracted organic solutions were combined, and then washed consecutively with water, saturated NaHCO3 aqueous solution, and salt water. The resultant solution was dried with anhydrous magnesium sulfate, and after filtering and evaporating the solvent, a yellow viscous liquid was obtained. Such liquid was recrystallized three times with a small amount of ethylacetate, and 11.1 g (yield: 45%) of a light yellow solid having the melting point of 108° C. to 109° C. was obtained. [1H-NMR (CDCl3), δ 3.48-3.56(m, 11H, OCH2 and OCH3), 3.98(t, 2H, OCH2), 4.61(t, 2H, NCH2), 7.62(d, 2H, aromatic), 8.13(d, 2H, aromatic), 8.68(s, 2H, aromatic), 10.15(s, 2H, CHO)].

Provenance & Evidence