Polyethyloxazoline

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

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

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

Procedure: As an example, step A was conducted by reacting 2-ethyl-2-oxazoline (4 moles) having less than 1,000 ppm of water with paraformaldehyde (1 mole) at a reaction temperature of 100° C. for approximately 5.5 hours. The excess oxazoline reactant was removed along with water as "overheads" by fractional distillation of the reaction product, leaving the 2-(α-hydroxymethylethyl)-2-oxazoline in approximately 96 percent yield. Step C was then conducted by continuously adding the 2-(α-hydroxymethylethyl)-2-oxazoline to a stirred solution of sodium hydroxide in the mono-methyl ether of triethylene glycol at a temperature of from 100°-105° C. Under these conditions, the 2-isopropenyl-2-oxazoline and water were volatilized and recovered from the overheads. The product yield was approximately 98 percent of theory. at a reaction temperature of 100° C. for approximately 5.5 hours The excess oxazoline reactant was removed along with water as "overheads" by fractional distillation of the reaction product

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 225 pounds of decylmercaptan are loaded into a jacketed reactor equipped with an agitator. 1.25 pounds of zinc chloride catalyst are added through the manhole. The system is heated to approximately 140° C. and 130 pounds of 2-ethyl-2-oxazoline are added at the rate of 3 lbs/min in about 45 minutes. About 30 minutes are allowed for the reaction to be completed, the reactor cooled to approximately 120° C. and 155 pounds of 32 weight percent hydrochloric acid are then added to the reaction mixture. The reactor is heated to 150°-160° C., at which time the vapor pressure of the system is approximately 60 psi. The temperature is maintained near 150° C. for 2 hours to complete the hydrolysis. equipped with an agitator About 30 minutes are allowed for the reaction the reactor cooled to approximately 120° C. The reactor is heated to 150°-160° C., at which time the vapor pressure of the system The temperature is maintained near 150° C. for 2 hours the hydrolysis

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

Procedure: To 25 g (0.25 mol) of 2-ethyl-4,5-dihydrooxazole add 10.0 g (62 mmol) of 4-(1H-imidazol-1-yl)phenol. Reflux the reaction mixture. Monitor the progress of the reaction by thin-layer chromatography on silica gel (9:1, CH2Cl2 :MeOH). Upon completion of the reaction remove the excess starting material by distillation, add ethyl acetate, and wash the solution with 2 N NaOH. Dry the organic layer over anhydrous Na2SO4. Remove the drying agent by filtration and remove the solvent in vacuo. Recrystallization from ethyl acetate-hexane affords the title compound. Reflux the reaction mixture Monitor the progress of the reaction by thin-layer chromatography on silica gel (9:1, CH2Cl2 :MeOH) Upon completion of the reaction remove the by distillation add ethyl acetate wash the solution with 2 N NaOH Dry the organic layer over anhydrous Na2SO4 Remove the drying agent by filtration remove the solvent in vacuo Recrystallization from ethyl acetate-hexane

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: C4F9SO2—N(CH3)CH2CH2—NH2 was prepared by the following procedure: N-Methylnonafluorobutanesulfonamide (626 g, 2 moles, 3M Company, St. Paul, Minn.), 2-ethyl-2-oxazoline (198 g, 2 moles, Alfa Aesar, Ward Hill, Mass.), and sodium carbonate (17 g, 0.16 mole, EMD Chemicals, Gibbstown, N.J.) were combined and heated for 16 hours at 140° C. to form N-(2-(N-methylnonafluorobutanesulfonamido)ethyl)propionamide. This amide was twice extracted with 250 mL deionized water, heated for 18 hours at 100° C. with a mixture of 250 mL concentrated hydrochloric acid and 100 mL deionized water, extracted with 925 mL of 24 weight percent aqueous sodium hydroxide solution, extracted with 250 mL 10 weight percent aqueous sodium hydroxide solution, and distilled to provide N-(2-aminoethyl)-N-methylnonafluorobutanesulfonamide (538 g; 75 percent recovery; 94 percent pure by gas chromatography (GC); distilled at 104-109° C. under 2 mm Hg pressure).

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: C4F9SO2—N(CH3)CH2CH2—NH2 was prepared by the following procedure: N-Methylnonafluorobutanesulfonamide (626 g, 2 moles, 3M Company, St. Paul, Minn.), 2-ethyl-2-oxazoline (198 g, 2 moles, Alfa Aesar, Ward Hill, Mass.), and sodium carbonate (17 g, 0.16 mole, EMD Chemicals, Gibbstown, N.J.) were combined and heated for 16 hours at 140° C. to form N-(2-(N-methylnonafluorobutanesulfonamido)ethyl)propionamide. This amide was twice extracted with 250 mL deionized water, heated for 18 hours at 100° C. with a mixture of 250 mL concentrated hydrochloric acid and 100 mL deionized water, extracted with 925 mL of 24 weight percent aqueous sodium hydroxide solution, extracted with 250 mL 10 weight percent aqueous sodium hydroxide solution, and distilled to provide N-(2-aminoethyl)-N-methylnonafluorobutanesulfonamide (538 g; 75 percent recovery; 94 percent pure by gas chromatography (GC); distilled at 104-109° C. under 2 mm Hg pressure).

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 225 pounds of decylmercaptan are loaded into a jacketed reactor equipped with an agitator. 1.25 pounds of zinc chloride catalyst are added through the manhole. The system is heated to approximately 140° C. and 130 pounds of 2-ethyl-2-oxazoline are added at the rate of 3 lbs/min in about 45 minutes. About 30 minutes are allowed for the reaction to be completed, the reactor cooled to approximately 120° C. and 155 pounds of 32 weight percent hydrochloric acid are then added to the reaction mixture. The reactor is heated to 150°-160° C., at which time the vapor pressure of the system is approximately 60 psi. The temperature is maintained near 150° C. for 2 hours to complete the hydrolysis. equipped with an agitator About 30 minutes are allowed for the reaction the reactor cooled to approximately 120° C. The reactor is heated to 150°-160° C., at which time the vapor pressure of the system The temperature is maintained near 150° C. for 2 hours the hydrolysis

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

Procedure: As an example, step A was conducted by reacting 2-ethyl-2-oxazoline (4 moles) having less than 1,000 ppm of water with paraformaldehyde (1 mole) at a reaction temperature of 100° C. for approximately 5.5 hours. The excess oxazoline reactant was removed along with water as "overheads" by fractional distillation of the reaction product, leaving the 2-(α-hydroxymethylethyl)-2-oxazoline in approximately 96 percent yield. Step C was then conducted by continuously adding the 2-(α-hydroxymethylethyl)-2-oxazoline to a stirred solution of sodium hydroxide in the mono-methyl ether of triethylene glycol at a temperature of from 100°-105° C. Under these conditions, the 2-isopropenyl-2-oxazoline and water were volatilized and recovered from the overheads. The product yield was approximately 98 percent of theory. at a reaction temperature of 100° C. for approximately 5.5 hours The excess oxazoline reactant was removed along with water as "overheads" by fractional distillation of the reaction product

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

Procedure: As an example, step A was conducted by reacting 2-ethyl-2-oxazoline (4 moles) having less than 1,000 ppm of water with paraformaldehyde (1 mole) at a reaction temperature of 100° C. for approximately 5.5 hours. The excess oxazoline reactant was removed along with water as "overheads" by fractional distillation of the reaction product, leaving the 2-(α-hydroxymethylethyl)-2-oxazoline in approximately 96 percent yield. Step C was then conducted by continuously adding the 2-(α-hydroxymethylethyl)-2-oxazoline to a stirred solution of sodium hydroxide in the mono-methyl ether of triethylene glycol at a temperature of from 100°-105° C. Under these conditions, the 2-isopropenyl-2-oxazoline and water were volatilized and recovered from the overheads. The product yield was approximately 98 percent of theory. at a reaction temperature of 100° C. for approximately 5.5 hours The excess oxazoline reactant was removed along with water as "overheads" by fractional distillation of the reaction product

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

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

Procedure: Under the same conditions as Example 13, 2.5 gm (25 mmoles) of 2-ethyl-2-oxazoline, 2.2 gm (25 mmoles) of morpholine and 0.59 mg of zinc acetate are reacted to yield 83 percent N-(2-morpholinylethyl)propionamide.