* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: 6-Hydroxy-2-naphthoic acid (1) (2.44 g, 13 mmol, 1 equiv.) and KOH (1.46 g, 26 mmol, 2equiv.) were dissolved in ethanol/water (25 mL, 9/1) and the solution was stirred for 20 min;corresponding n-alkyl bromide (32.50 mmol, 2.5 equiv.) was then added and the mixture isheated under reflux for 24 hr. When the reaction was complete, KOH (0.73 g, 13 mmol, 1equiv.) was added and the mixture is heated under reflux for further 4 hr. The ethanol wasevaporated, and the mixture is poured into water and acidified to approximately pH = 2?3with acetic acid. The precipitatewas filtered and washed with water and ether, and then recrystallizedtwice from glacial acetic acid, then from ethanol to give 71%?80% yield. (IR) (KBr):upsilonmax/cm-1: 3061, 2930, 2828, 1680, 1603, 1311, 1472, 1450, 1383, 1216, 1060, and 721.
4-(5-Octylsulfanyl-[1,3,4]oxadiazol-2-yl)-phenol[ No CAS ]
C29H32N2O4S[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20.0℃; for 24h;
General procedure: A compound 4-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)phenol (7) (1.8 mmol, 1 equiv.), corresponding6-alkoxy-2-naphthoic acid (1.8 mmol, 1 equiv.) and DMAP (0.008 g, 0.08 mmol,0.05 equiv.) were stirred in anhydrous CH2Cl2 (10 mL). To this solution, DCC (0.56 g, 2.7 mmol, 1.5 equiv.) in CH2Cl2 (2 mL) added slowly at room temperature and the mixturewas stirred for 24 hr at room temperature. After the completion of the reaction, the whitesolid N,N?-dicyclohexylure was filtered off; the filtrate was diluted with CH2Cl2 (20mL), thenwas washed thoroughly with 4% HCl, saturated NaHCO3 and twice with water. The organiclayer was separated, dried over Na2SO4, and evaporated. The product was purified by columnchromatography over silica gel (60-120 mesh), using 40% hexane:ethyl acetate as eluent andrecrystallized from the solvent mixture dichloromethane:ethanol (1:9) obtain slight brownsolid (yield: 83-91%) [61-63].
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20.0℃; for 24h;
General procedure: A compound 4-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)phenol (7) (1.8 mmol, 1 equiv.), corresponding6-alkoxy-2-naphthoic acid (1.8 mmol, 1 equiv.) and DMAP (0.008 g, 0.08 mmol,0.05 equiv.) were stirred in anhydrous CH2Cl2 (10 mL). To this solution, DCC (0.56 g, 2.7 mmol, 1.5 equiv.) in CH2Cl2 (2 mL) added slowly at room temperature and the mixturewas stirred for 24 hr at room temperature. After the completion of the reaction, the whitesolid N,N?-dicyclohexylure was filtered off; the filtrate was diluted with CH2Cl2 (20mL), thenwas washed thoroughly with 4% HCl, saturated NaHCO3 and twice with water. The organiclayer was separated, dried over Na2SO4, and evaporated. The product was purified by columnchromatography over silica gel (60-120 mesh), using 40% hexane:ethyl acetate as eluent andrecrystallized from the solvent mixture dichloromethane:ethanol (1:9) obtain slight brownsolid (yield: 83-91%) [61-63].
bis{4-[5-(6-ethoxynaphthalen-2-yl)-1,3,4-oxadiazol-2-yl]phenyl}dimethylsilane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
35%
With trichlorophosphate; for 16h;Inert atmosphere; Reflux;
A mixture of the appropriate 2-naphthoic acid 6a-d (2 mmol), 4,4?-(dimethylsilanediyl)di(benzohydrazide) (1 mmol), and phosphorus oxychloride (10 mL) was heated under reflux for 16 h under N2, then cooled to room temperature, and poured onto crushed ice. The resulting dark green solid precipitate was filtered and then washed thoroughly with distilled ice water. The solid was recrystallized from DMF/H2O to obtainthe pure final compound.