4-ethenylaniline

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: Dehydration of 9.2 g of p-aminophenylethanol (Chem. Abs., vol. 59:3797f) was done by heating with 8.8 g of KOH in the flame of a Bunsen burner under a nitrogen atmosphere (about 6 mm pressure). The product was collected by cooling with a Dry Ice-acetone bath. The solution was extracted with ether, dried over KOH and filtered. Evaporation of the ether gave p-aminostyrene, which was characterized by IR and NMR; the yield was 6.4 g. flame of a Bunsen burner under a nitrogen atmosphere (about 6 mm pressure) The product was collected by cooling with a Dry Ice-acetone bath The solution was extracted with ether dried over KOH filtered Evaporation of the ether

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

Procedure: A copolymer of 2-vinyl pyridine and para-aminostyrene was prepared in a similar manner to example A with the exception that toluene was used instead of ethanol and only 2.80 ml of para-aminostyrene was used. The resultant product was purified by allowing the toluene to evaporate, redissolving the precipitate in dioxin and reprecipitating with water. The resultant polymer had a number average molecular weight of about 21,500 and a weight average molecular weight of about 54,000 as determined by GPC. The resultant product was purified to evaporate redissolving the precipitate in dioxin reprecipitating with water

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

Procedure: Dehydration of 9.2 g of p-aminophenylethanol (Chem. Abs., vol. 59:3797f) was done by heating with 8.8 g of KOH in the flame of a Bunsen burner under a nitrogen atmosphere (about 6 mm pressure). The product was collected by cooling with a Dry Ice-acetone bath. The solution was extracted with ether, dried over KOH and filtered. Evaporation of the ether gave p-aminostyrene, which was characterized by IR and NMR; the yield was 6.4 g. flame of a Bunsen burner under a nitrogen atmosphere (about 6 mm pressure) The product was collected by cooling with a Dry Ice-acetone bath The solution was extracted with ether dried over KOH filtered Evaporation of the ether

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

Procedure: 11.4 g of sodium nitrite, 28.0 g of sulfanilic acid and 1200 g of 0° C. water were fed into a reactor to form diazonium sulfanilate, to which was added 200 g of a carbon black pigment, Raven C. When the generation of nitrogen ceased, the reaction mixture was concentrated, and further reacted at an elevated temperature. The resulting mixture was extracted with ethanol for 12 hours in a Soxhlet's extractor to remove unreacted compounds and side products, and this was again dissolved in water and filtered to obtain a dispersion of about 20 wt. % sulfanilate-processed carbon black pigment. On the other hand, 3.6 g of aminostyrene, 2.1 g of sodium nitrite and 150 g of water were fed into a separate reactor to form a diazonium salt of 4-aminostyrene, and this was dissolved in 10 g of ethanol. The sulfanilate-processed carbon black pigment dispersion was added to the diazonium salt solution and reacted for 18 hours with stirring. Then, this was filtered and purified through Soxhlet extraction to obtain a dispersion of a carbon black pigment having 4-aminostyrene added to its surface. Next, 30 g of deionized water was degassed in a nitrogen atmosphere at 90° C. in a reactor, and a mixture of 28.13 g of the 4-aminostyrene-added carbon black pigment dispersion, 2.0 g of methyl methacrylate, 2.0 g of butyl acrylate, and 1.0 g of polyethylene glycol 2000 monomethyl ether acrylate dissolved in 3.0 g of deionized water was dropwise added thereto over a period of 20 minutes. 0.22 g of potassium persulfate was added thereto and reacted at 80° C. for 18 hours. The resulting product was concentrated under reduced pressure, and extracted with acetone in an Soxhlet's extractor to remove the non-added polymer. The process gave an intended dispersion of a pigment having a polymer group bonded to its surface.

Conditions: temp:240.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-(4-aminophenyl)ethanol (10 g, 73 mmol), KOH (25 g, 450 mmol) and t butylcatechol (0.1 g) was heated at 240° C./40 mmHg in a flask fitted with a water-cooled condenser for 90 minutes. The contents of the flask were then distilled into a receiver vessel as a clear, 2-phase system which sodified as white crystals on standing. The solid was extracted with 50 ml diethyl ether, washed twice with 25 ml distilled water and the organic phase separated. After drying for 2 hours over NaOH pellets, the ether solution was filtered and the volatiles removed in vacuo to yield a colourless crystalline solid. Fractional distillation at 38° C. (1×10-2 mbar) yielded 4-aminostyrene. The colourless liquid was stored at -30° C. (at which temperature it is a crystalline solid) to prevent polymerisation. cooled condenser for 90 minutes The contents of the flask were then distilled into a receiver vessel as a clear, 2-phase system which The solid was extracted with 50 ml diethyl ether washed twice with 25 ml distilled water the organic phase separated After drying for 2 hours over NaOH pellets the ether solution was filtered the volatiles removed in vacuo to yield a colourless crystalline solid Fractional distillation at 38° C. (1×10-2 mbar)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 ml flask was charged with CH2Cl2 (24 ml) under nitrogen stream and stirred for 10 min at 0° C. and then 2-(fluorosulfonyl)difluoroacetyl fluoride (6.60 g, 37.6 mmol, 1.5 eq.) was added. After 20 minutes, the CH2Cl2 (12 ml) solution of 4-vinyl aniline (2.86 g, 24.4 mmol, 1.0 eq.) and pyridine (1.93 g, 24.4 mmol, 1.0 eq.) was added dropwise to the mixture over 10 minutes. The mixture was allowed to warm to RT and was stirred for 4 hours at RT. 1N HCl was added to the final reaction mixture and the lower layer was separated and washed with 1N HCl and brine. The solution was dried over MgSO4, filtrated and then CH2Cl2 was removed by an evaporator. The target compound was obtained as a white solid (6.57 g) in 96% yield. 1H NMR (400 MHz, CDCl3); delta=5.28 (d, J=10.9 Hz, 1H), 5.74 (d, J=17.6 Hz, 1H), 6.68 (dd, J=10.9, 17.6 Hz, 1H), 7.43 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.7 Hz, 2H), 8.04 (brs, 1H). 19F-NMR (376 MHz, CDCl3, C6F6 as standard) delta=41.27 (t, J=4.6 Hz, 1F), −105.26 (d, J=4.2 Hz, 2F). After 20 minutes to warm to RT was stirred for 4 hours at RT reaction mixture the lower layer was separated washed with 1N HCl and brine The solution was dried over MgSO4 filtrated CH2Cl2 was removed by an evaporator

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

Procedure: To a stirred solution of 4-aminostyrene (3.5 mmol) in dry THF (20 mL) under nitrogen was added 3,5-bis-(trifluoromethyl)phenyl isothiocyanate (3.5 mmol). The solution was refluxed overnight and then the solvent was evaporated under reduced pressure. The resulting solid residue was purified by column chromatography to yield the desired product in 60% yield. The solution was refluxed overnight the solvent was evaporated under reduced pressure The resulting solid residue was purified by column chromatography

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

Procedure: To a stirred solution of 4-aminostyrene (3.5 mmol) in dry THF (20 mL) under nitrogen was added 3,5-bis-(trifluoromethyl)phenyl isothiocyanate (3.5 mmol). The solution was refluxed overnight and then the solvent was evaporated under reduced pressure. The resulting solid residue was purified by column chromatography to yield the desired product in 60% yield. The solution was refluxed overnight the solvent was evaporated under reduced pressure The resulting solid residue was purified by column chromatography

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

Procedure: To a solution of 500 g (4.2 moles) of 4-vinylaniline and 460 g (4.2 moles) of triethylamine in 1000 cc of anhydrous diethyl ether under a nitrogen atmosphere was added dropwise 478 g (4.2 moles) of methanesulfonyl chloride. The temperature of the reaction vessel was kept below 5° C by an ice bath during the course of the reaction. When addition was complete (40 min.), the mixture was stirred for an additional 2 hours and the contents of the flask then brought to room temperature. The mixture was filtered and extracted with 500 cc of 1.0 M HCl solution. The etheral portion was separated, dried and the ether removed on a rotary evaporator. The resulting oily solid was extracted with 500 cc of ethanol and recrystallized from ethane/water and then from toluene. 70-75% yield after recrystallization. M.P. = 97° C. The temperature of the reaction vessel was kept below 5° C by an ice bath during the course of the reaction When addition (40 min.) then brought to room temperature The mixture was filtered extracted with 500 cc of 1.0 M HCl solution The etheral portion was separated dried the ether removed on a rotary evaporator The resulting oily solid was extracted with 500 cc of ethanol recrystallized from ethane/water 70-75% yield after recrystallization

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

Procedure: To a solution of 500 g (4.2 moles) of 4-vinylaniline and 460 g (4.2 moles) of triethylamine in 1000 cc of anhydrous diethyl ether under a nitrogen atmosphere was added dropwise 478 g (4.2 moles) of methanesulfonyl chloride. The temperature of the reaction vessel was kept below 5° C. by an ice bath during the course of the reaction. When addition was complete (40 min.), the mixture was stirred for an additional 2 hours and the contents of the flask then brought to room temperature. The mixture was filtered and extracted with 500 cc of 1.0 M HCl solution. The etheral portion was separated, dried and the ether removed on a rotary evaporator. The resulting oily solid was extracted with 500 cc of ethanol and recrystallized from ethane/water and then from toluene. 70-75% yield after recrystallization. M.P. = 97° C. The temperature of the reaction vessel was kept below 5° C. by an ice bath during the course of the reaction When addition (40 min.) then brought to room temperature The mixture was filtered extracted with 500 cc of 1.0 M HCl solution The etheral portion was separated dried the ether removed on a rotary evaporator The resulting oily solid was extracted with 500 cc of ethanol recrystallized from ethane/water 70-75% yield after recrystallization