2-[butyl(2-hydroxyethyl)amino]ethanol

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of (2-methoxycarbonylphenyl)boronic acid (5.0 g, 27.8 mmol) in toluene (40 mL) was added N-butyldiethanolamine (4.8 mL, 29.2 mmol, 1.05 equiv.) via a syringe. The mixture was heated at 50° C. for two hours. After cooling to room temperature, the toluene was evaporated under reduced pressure and the remaining clear colorless crude oil was treated with heptanes (˜500 mL). The heptanes mixture was then sonicated ˜5 min and the resulting suspension was allowed to stand at room temperature overnight. The solid that precipitated was collected by filtration, washed with heptanes, and dried in a vacuum oven overnight to yield a white solid as the 2-(2′-methoxycarbonylphenyl)-6-butyl[1,3,6,2]dioxazaborocan. 1H NMR (DMSO-d6) δ: 7.55-7.59 (m, 1H), 7.17-7.29 (m, 2H), 7.12-7.14 (m, 1H), 3.85-3.92 (m, 2H), 3.78-3.82 (m, 1H), 3.78 (br. s., 1H), 3.67 (s, 3H), 3.26-3.30 (m, 1H), 3.12 (dt, J=5.2, 2.6 Hz, 2H), 3.03-3.11 (m, 2H), 2.41-2.49 (m, 4H), 1.45-1.55 (m, 2H), 0.98-1.05 (m, 2H), 0.83 (s, 1H), 0.71-0.77 (m, 3H). Amount obtained, 8.3 g, (98.1% yield). After cooling to room temperature the toluene was evaporated under reduced pressure the remaining clear colorless crude oil was treated with heptanes (˜500 mL) The heptanes mixture was then sonicated ˜5 min The solid that precipitated was collected by filtration washed with heptanes dried in a vacuum oven overnight

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of (2-methoxycarbonylphenyl)boronic acid (5.0 g, 27.8 mmol) in toluene (40 mL) was added N-butyldiethanolamine (4.8 mL, 29.2 mmol, 1.05 equiv.) via a syringe. The mixture was heated at 50° C. for two hours. After cooling to room temperature, the toluene was evaporated under reduced pressure and the remaining clear colorless crude oil was treated with heptanes (˜500 mL). The heptanes mixture was then sonicated ˜5 min and the resulting suspension was allowed to stand at room temperature overnight. The solid that precipitated was collected by filtration, washed with heptanes, and dried in a vacuum oven overnight to yield a white solid as the 2-(2′-methoxycarbonylphenyl)-6-butyl[1,3,6,2]dioxazaborocan. 1H NMR (DMSO-d6) δ: 7.55-7.59 (m, 1H), 7.17-7.29 (m, 2H), 7.12-7.14 (m, 1H), 3.85-3.92 (m, 2H), 3.78-3.82 (m, 1H), 3.78 (br. s., 1H), 3.67 (s, 3H), 3.26-3.30 (m, 1H), 3.12 (dt, J=5.2, 2.6 Hz, 2H), 3.03-3.11 (m, 2H), 2.41-2.49 (m, 4H), 1.45-1.55 (m, 2H), 0.98-1.05 (m, 2H), 0.83 (s, 1H), 0.71-0.77 (m, 3H). Amount obtained, 8.3 g, (98.1% yield). After cooling to room temperature the toluene was evaporated under reduced pressure the remaining clear colorless crude oil was treated with heptanes (˜500 mL) The heptanes mixture was then sonicated ˜5 min The solid that precipitated was collected by filtration washed with heptanes dried in a vacuum oven overnight

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

Procedure: 1.0 mol of isophorone diisocyanate is dissolved in 2.2 mol of phenol at 95°-100° C. after the addition of 0.5 imidazole. The mixture is kept as a liquid by the addition of 200 ml of ethylglycol acetate. 0.9 mol of butyldiethanolamine are added after a reaction time of four hours and the mixture is then distilled at a reaction temperature of 120° C. to remove everything which distils off at a vacuum of 5 torr. The residue is then dissolved in 200 ml of ethylglycol acetate and 400 ml of ethanol and quaternised at 60°-70° C., first with 0.5 mol of epichlorohydrin for three hours and then with 0.5 mol of diethylsulphate. The readily soluble cationic polyurethane with phenylurethane end groups obtained in this way is made up to a volume of 2000 ml with methanol and then stored at temperatures below 10° C. the mixture is then distilled at a reaction temperature of 120° C. to remove everything which distils off at a vacuum of 5 torr The residue is then dissolved in 200 ml of ethylglycol acetate

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

Procedure: The procedure of Example 1 was followed using N-butyl diethanolamine (13.5 g, 83.9 mmol), triethylamine (24.0 mL, 167.8 mmol), dry THF (600 mL) and triphosgene (8.3 g, 28.8 mmol). The filtrate was concentrated yielding a yellow/brown oil product (12.9 g, 82%). The filtrate was concentrated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of (2-methoxycarbonylphenyl)boronic acid (5.0 g, 27.8 mmol) in toluene (40 mL) was added N-butyldiethanolamine (4.8 mL, 29.2 mmol, 1.05 equiv.) via a syringe. The mixture was heated at 50° C. for two hours. After cooling to room temperature, the toluene was evaporated under reduced pressure and the remaining clear colorless crude oil was treated with heptanes (˜500 mL). The heptanes mixture was then sonicated ˜5 min and the resulting suspension was allowed to stand at room temperature overnight. The solid that precipitated was collected by filtration, washed with heptanes, and dried in a vacuum oven overnight to yield a white solid as the 2-(2′-methoxycarbonylphenyl)-6-butyl[1,3,6,2]dioxazaborocan. 1H NMR (DMSO-d6) δ: 7.55-7.59 (m, 1H), 7.17-7.29 (m, 2H), 7.12-7.14 (m, 1H), 3.85-3.92 (m, 2H), 3.78-3.82 (m, 1H), 3.78 (br. s., 1H), 3.67 (s, 3H), 3.26-3.30 (m, 1H), 3.12 (dt, J=5.2, 2.6 Hz, 2H), 3.03-3.11 (m, 2H), 2.41-2.49 (m, 4H), 1.45-1.55 (m, 2H), 0.98-1.05 (m, 2H), 0.83 (s, 1H), 0.71-0.77 (m, 3H). Amount obtained, 8.3 g, (98.1% yield). After cooling to room temperature the toluene was evaporated under reduced pressure the remaining clear colorless crude oil was treated with heptanes (˜500 mL) The heptanes mixture was then sonicated ˜5 min The solid that precipitated was collected by filtration washed with heptanes dried in a vacuum oven overnight