Water → HCID 118869905, compound

Participants

Reaction Conditions

Reaction Steps

10 g (37.3 mmol) of 4-((2-hydroxy-4-nitrophenyl)diazenyl)benzonitrile is dissolved in 200 mL of acetone, and 7.8 mL (44.9 mmol) of 1-bromooctane and 10.3 g (74.5 mmol) of potassium carbonate (K2CO3) are added thereto. Subsequently, the resultant reaction mixture is agitated at 60° C. for 24 hours while being refluxed, and then the temperature is lowered to room temperature. The reaction mixture is concentrated, dissolved in dichloromethane (CH2Cl2), passes through a silica gel pad, and the filtrated solution is recrystallized using dichloromethane (CH2Cl2) and n-hexane. The purified compound is dissolved in 150 mL of hot ethanol, and 12.5 g (74.4 mmol) of Na2S.5H2O dissolved in hot ethanol and water is added thereto. Subsequently the resultant reaction mixture is agitated at 80° C. for 5 hours, and then the temperature is lowered to room temperature. The resultant precipitated crystal is filtered, washed with water several times, and dried, thus obtaining 8.9 g (25.4 mmol) of 4-((4-amino-2-(octyloxy)phenyl)diazenyl)benzonitrile of the following Chemical Formula 1a-1. A yield is 68%.

Provenance & Evidence