1-chlorohexadecane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.6 g of 5-fluorouracil was suspended in 20 ml of absolute dioxane and 10 ml of absolute pyridine, and 15 g of palmityl chloride was added to the suspension followed by heating at 80° C for 1 hour while stirring. After completion of the reaction, the solvent was removed under reduced pressure (25 mm Hg), and the residual solid was washed with hot hexane (50° C). Any insoluble matter in the hot hexane was recrystallized from benzene to obtain 4.0 g of 1-N-palmitoyl-5-fluorouracil in a yield of 54%. Melting Point: 98° C. After completion of the reaction the solvent was removed under reduced pressure (25 mm Hg) the residual solid was washed with hot hexane (50° C) Any insoluble matter in the hot hexane was recrystallized from benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a refluxing mixture of 1.26 g of magnesium turnings, 15.5 ml of 1-chlorohexadecane, and 100 ml of anhydrous diethyl ether were added 0.5 ml of a 3.2M solution of methylmagnesium bromide in diethyl ether and 0.05 ml of ethyl bromide. The reaction mixture was refluxed for a period of 6 hours. A solution of 3.0 g of 4-[(tetrahydro-2H-pyran-2-yl)oxy]butanal in 10 ml of diethyl ether was added, and the reaction mixture refluxed for an additional hour. The reaction mixture was poured into a mixture of ice and a saturated aqueous solution of ammonium chloride, and filtered. Upon standing the filtrate separated into organic and inorganic phases. The organic phase was dried over anhydrous sodium sulfate and concentrated to an oil. Flash chromatography of the oil utilizing 25% diethyl ether/petroleum ether yielded 4.8 g (70%) of 1-[(tetrahydro-2H-pyran-2-yl)oxy]eicosan-4-ol as a solid, mp 39°-43°. The reaction mixture was refluxed for a period of 6 hours the reaction mixture refluxed for an additional hour The reaction mixture was poured into a mixture of ice a saturated aqueous solution of ammonium chloride, and filtered separated into organic and inorganic phases The organic phase was dried over anhydrous sodium sulfate concentrated to an oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 ml capacity conical flask 13 g cetyl chloride (0.05 M), 3.5 g acrylamide (0.05 M) and 50 ml acetone were placed to obtain a clear solution. The solution was stirred with a magnetic needle at room temperature. 6.5 g anhydrous aluminium chloride (0.05 M) was added and the reaction mixture was stirred at room temperature. After 5 to 10 minutes of stirring, vigorous evolution of hydrogen chloride took place which ceased after about 5 minutes. Temperature of the reaction mixture was raised to 40 to 50° C. It was then cooled to room temperature and poured into 500 ml cold water. White product was precipitated. The product was isolated and purified by reprecipitation from acetone into cold water. to obtain a clear solution the reaction mixture was stirred at room temperature After 5 to 10 minutes of stirring Temperature of the reaction mixture was raised to 40 to 50° C It was then cooled to room temperature White product was precipitated The product was isolated purified by reprecipitation from acetone into cold water

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 2 L three-necked round bottom flask equipped with overhead mechanical stirrer were added 1-chlorohexadecane (260 g, 1.00 moles), 1,2 dimethylimidazole (91.0 g, 0.95 moles), and CH3CN (500 mL) and the two-phase reaction mixture was vigorously stirred in an oil bath at 80° C. After 72 h, the reaction mixture was cooled to room temperature and the product was crystallized overnight. The crystallized solid was filtered, thoroughly washed with cold CH3CN, and vacuum dried at 70° C. for 3 days to give 1,2-dimethyl-3-hexadecylimidazolium chloride as a slightly off-white solid, 220 g, 62% yield. To a 2 L three-necked round bottom flask equipped with overhead mechanical stirrer the two-phase reaction mixture the reaction mixture was cooled to room temperature the product was crystallized overnight The crystallized solid was filtered thoroughly washed with cold CH3CN, and vacuum dried at 70° C. for 3 days

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 2 L three-necked round bottom flask equipped with overhead mechanical stirrer were added 1-chlorohexadecane (260 g, 1.00 moles), 1,2 dimethylimidazole (91.0 g, 0.95 moles), and CH3CN (500 mL) and the two-phase reaction mixture was vigorously stirred in an oil bath at 80° C. After 72 h, the reaction mixture was cooled to room temperature and the product was crystallized overnight. The crystallized solid was filtered, thoroughly washed with cold CH3CN, and vacuum dried at 70° C. for 3 days to give 1,2-dimethyl-3-hexadecylimidazolium chloride as a slightly off-white solid, 220 g, 62% yield. To a 2 L three-necked round bottom flask equipped with overhead mechanical stirrer the two-phase reaction mixture the reaction mixture was cooled to room temperature the product was crystallized overnight The crystallized solid was filtered thoroughly washed with cold CH3CN, and vacuum dried at 70° C. for 3 days

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.6 g of 5-fluorouracil was suspended in 20 ml of absolute dioxane and 10 ml of absolute pyridine, and 15 g of palmityl chloride was added to the suspension followed by heating at 80° C for 1 hour while stirring. After completion of the reaction, the solvent was removed under reduced pressure (25 mm Hg), and the residual solid was washed with hot hexane (50° C). Any insoluble matter in the hot hexane was recrystallized from benzene to obtain 4.0 g of 1-N-palmitoyl-5-fluorouracil in a yield of 54%. Melting Point: 98° C. After completion of the reaction the solvent was removed under reduced pressure (25 mm Hg) the residual solid was washed with hot hexane (50° C) Any insoluble matter in the hot hexane was recrystallized from benzene

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 120 parts of phenol, 6.1 parts (0.1 mole) of boric acid and 70 parts of toluene are refluxed, while stirring, the water of reaction formed thereby being removed from the system. The toluene is then distilled off, the mixture is cooled to 110° C. and 25.4 parts (0.05 mole) of 1-palmitylamino-8-amino-4,5-dihydroxyanthraquinone (prepared by reacting 1-amino-8-nitro-4,5-dihydroxyanthraquinone with palmityl chloride in nitrobenzene and then reducing the product with hydrazine hydrate) are added. Ammonia is then passed in at this temperature until no further starting material can be detected in the thin-layer chromatogram (duration: 3 hours). The reaction mixture is cooled to 90° C. and 240 parts of methanol are added. After cooling to room temperature, the dye precipitated is filtered off with suction and the material on the filter is washed with methanol and water and dried. 20 parts of 1,4-diamino-5-hydroxy-8-palmitylaminoanthraquinone of melting point 174° C. are obtained. formed thereby being removed from the system The toluene is then distilled off are added The reaction mixture is cooled to 90° C. After cooling to room temperature the dye precipitated is filtered off with suction the material on the filter is washed with methanol and water dried

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 120 parts of phenol, 6.1 parts (0.1 mole) of boric acid and 70 parts of toluene are refluxed, while stirring, the water of reaction formed thereby being removed from the system. The toluene is then distilled off, the mixture is cooled to 110° C. and 25.4 parts (0.05 mole) of 1-palmitylamino-8-amino-4,5-dihydroxyanthraquinone (prepared by reacting 1-amino-8-nitro-4,5-dihydroxyanthraquinone with palmityl chloride in nitrobenzene and then reducing the product with hydrazine hydrate) are added. Ammonia is then passed in at this temperature until no further starting material can be detected in the thin-layer chromatogram (duration: 3 hours). The reaction mixture is cooled to 90° C. and 240 parts of methanol are added. After cooling to room temperature, the dye precipitated is filtered off with suction and the material on the filter is washed with methanol and water and dried. 20 parts of 1,4-diamino-5-hydroxy-8-palmitylaminoanthraquinone of melting point 174° C. are obtained. formed thereby being removed from the system The toluene is then distilled off are added The reaction mixture is cooled to 90° C. After cooling to room temperature the dye precipitated is filtered off with suction the material on the filter is washed with methanol and water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of Example 74 (100.0 mg, 0.303 mmol), triethylamine (0.055 mL, 0.394 mmol), and cetyl chloride (0.024 mL, 0.334 mmol) in DMF (2.2 mL) was stirred at 0° C. for 60 minutes. Water was added slowly to the reaction mixture and a white suspension formed. The suspension was filtered, washed with water and diethyl ether, and oven-dried to give 45.0 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 0.87 (s, 6H), 1.89 (s, 3H), 2.96 (d, J=6.44 Hz, 2H), 3.13 (d, J=6.10 Hz, 2H), 6.86 (t, J=6.27 Hz, 1H), 6.90 (d, J=1.36 Hz, 1H), 6.98 (s, 1H), 7.22 (dd, J=7.80, 4.75 Hz, 1H), 7.79 (t, J=6.27 Hz, 1H), 8.15 (d, J=2.37 Hz, 1H), 8.27-8.40 (m, 2H), 12.16 (s, 1H). MS (ESI+) m/z 372.0 (M+H)+. a white suspension formed The suspension was filtered washed with water and diethyl ether oven-dried

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 2L three-necked round bottom flask equipped with overhead mechanical stirrer were added 1-chlorohexadecane (260 g, 1.00 moles), 1,2 dimethylimidazole (91.0 g, 0.95 moles), and CH3CN (500 mL) and the two-phase reaction mixture was vigorously stirred in an oil bath at 80° C. After 72 h, the reaction mixture was cooled to room temperature and the product was crystallized overnight. The crystallized solid was filtered, thoroughly washed with cold CH3CN, and vacuum dried at 70° C. for 3 days to give 1,2-dimethyl-3-hexadecylimidazolium chloride as a slightly off-white solid, 220 g, 62% yield. the two-phase reaction mixture the reaction mixture was cooled to room temperature the product was crystallized overnight The crystallized solid was filtered thoroughly washed with cold CH3CN, and vacuum dried at 70° C. for 3 days