4-hexylaniline

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: 1.7 g of 3-n-hexylisoxazol-5(4H)-one (prepared in accordance with Example 3) are dissolved in 10 ml of triethyl orthoformate and heated at 80° C. for 2 hours together with 2.65 g of p-hexylaniline. The dark reaction solution is concentrated and recrystallized in 100 ml of hexane. 1.8 g (50% of theory) of the above-named crystalline compound are obtained. M.p. 88°-90° C., UV (EtOH): 356 nm (ε=26469). This compound is especially suitable as a UV A filter. The dark reaction solution is concentrated recrystallized in 100 ml of hexane 1.8 g (50% of theory) of the above-named crystalline compound are obtained

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

Procedure: In a 2 liter-reaction vessel, 50.0 g (0.28 M) of p-hexylaniline, 54.8 g (0.56 M) of potassium thiocyanate and 400 ml of acetic acid were placed and cooled below 10° C. To the mixture, a solution of 45.0 g of bromine in 135 ml of acetic acid was added dropwise in 40 minutes below 10° C. under strong stirring, followed by reaction for 1.5 hours below 10° C. After the reaction, 500 ml of water was poured into the reaction mixture, followed by heating to dissolve the resultant precipitate. The resultant solution was filtered under heating. Ammonia water was added to the filtrate until the resultant solution became basic, followed by cooling with ice to precipitate a crystal. The crystal was recovered by filtration, followed by washing and drying to obtain a crude product. The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1) to obtain 33.0 g of 2-amino-6-hexylbenzothiazole (Yield: 49.9%). cooled below 10° C followed by reaction for 1.5 hours below 10° C was poured into the reaction mixture by heating The resultant solution was filtered under heating Ammonia water was added to the filtrate until the resultant solution by cooling with ice to precipitate a crystal The crystal was recovered by filtration by washing drying to obtain a crude product The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1)

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

Procedure: In a 2 liter-reaction vessel, 50.0 g (0.28M) of p-hexylaniline, 54.8 g (0.56M) of potassium thiocyanate and 400 ml of acetic acid were placed and cooled below 10° C. To the mixture, a solution of 45.0 g of bromine in 135 ml of acetic acid was added dropwise in 40 minutes below 10° C. under strong stirring, followed by reaction for 1.5 hours below 10° C. After the reaction, 500 ml of water was poured into the reaction mixture, followed by heating to dissolve the resultant precipitate. The resultant solution was filtered under heating. Ammonia water was added to the filtrate until the resultant solution became basic, followed by cooling with ice to precipitate a crystal. The crystal was recovered by filtration, followed by washing and drying to obtain a crude product. The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1) to obtain 33.0 g of 2-amino-6-hexylbenzothiazole (Yield: 49.9 %). cooled below 10° C followed by reaction for 1.5 hours below 10° C was poured into the reaction mixture by heating The resultant solution was filtered under heating Ammonia water was added to the filtrate until the resultant solution by cooling with ice to precipitate a crystal The crystal was recovered by filtration by washing drying to obtain a crude product The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1)

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

Procedure: In a 2 liter-reaction vessel, 50.0 g (0.28M) of p-hexylaniline, 54.8 g (0.56M) of potassium thiocyanate and 400 ml of acetic acid were placed and cooled below 10° C. To the mixture, a solution of 45.0 g of bromine in 135 ml of acetic acid was added dropwise in 40 minutes below 10° C. under strong stirring, followed by reaction for 1.5 hours below 10° C. After the reaction, 500 ml of water was poured into the reaction mixture, followed by heating to dissolve the resultant precipitate. The resultant solution was filtered under heating. Ammonia water was added to the filtrate until the resultant solution became basic, followed by cooling with ice to precipitate a crystal. The crystal was recovered by filtration, followed by washing and drying to obtain a crude product. The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1) to obtain 33.0 g of 2-amino-6-hexylbenzothiazole (Yield: 49.9 %). cooled below 10° C followed by reaction for 1.5 hours below 10° C was poured into the reaction mixture by heating The resultant solution was filtered under heating Ammonia water was added to the filtrate until the resultant solution by cooling with ice to precipitate a crystal The crystal was recovered by filtration by washing drying to obtain a crude product The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1)

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

Procedure: 30.1 g (0.17 M) of 4-hexylaniline was cooled to 0° C. or below, 85 gof 10% aqueous hydrochloric acid solution was added, and then a solution of11.6 g of sodium nitrite in 68 g of water was added. During the addition, the mixture was cooled so as not to exceed 0° C. After the addition, the mixture was allowed to react for 30 minutes, transferred into a dropping funnel and added dropwise into 170 g of an 8% NaOH aqueoussolution containing 16 g of phenol held at 5° C. or below. After theaddition, the mixture was stirred for 0.5 hour, and then 10% hydrochloric acid aqueous solution was added thereto until a pH of 5-6 to precipitate the reaction product. The precipitate was separated by filtration, washed with water and dried overnight under reduced pressure. After the drying, the product was washed with 500 ml of petroleum ether and further dried under reduced pressure to obtain 29.6 g (0.10M) of 4-hydroxy-4'-hexylazobenzene. The yield was 59%. During the addition the mixture was cooled so as not to exceed 0° C After the addition to react for 30 minutes transferred into a dropping funnel held at 5° C. or below until a pH of 5-6 to precipitate the reaction product The precipitate was separated by filtration washed with water dried overnight under reduced pressure After the drying, the product was washed with 500 ml of petroleum ether further dried under reduced pressure

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

Procedure: 1.7 g of 3-n-hexylisoxazol-5(4H)-one (prepared in accordance with Example 3) are dissolved in 10 ml of triethyl orthoformate and heated at 80° C. for 2 hours together with 2.65 g of p-hexylaniline. The dark reaction solution is concentrated and recrystallized in 100 ml of hexane. 1.8 g (50% of theory) of the above-named crystalline compound are obtained. M.p. 88°-90° C., UV (EtOH): 356 nm (ε=26469). This compound is especially suitable as a UV A filter. The dark reaction solution is concentrated recrystallized in 100 ml of hexane 1.8 g (50% of theory) of the above-named crystalline compound are obtained

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

Procedure: In a 2 liter-reaction vessel, 50.0 g (0.28 M) of p-hexylaniline, 54.8 g (0.56 M) of potassium thiocyanate and 400 ml of acetic acid were placed and cooled below 10° C. To the mixture, a solution of 45.0 g of bromine in 135 ml of acetic acid was added dropwise in 40 minutes below 10° C. under strong stirring, followed by reaction for 1.5 hours below 10° C. After the reaction, 500 ml of water was poured into the reaction mixture, followed by heating to dissolve the resultant precipitate. The resultant solution was filtered under heating. Ammonia water was added to the filtrate until the resultant solution became basic, followed by cooling with ice to precipitate a crystal. The crystal was recovered by filtration, followed by washing and drying to obtain a crude product. The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1) to obtain 33.0 g of 2-amino-6-hexylbenzothiazole (Yield: 49.9%). cooled below 10° C followed by reaction for 1.5 hours below 10° C was poured into the reaction mixture by heating The resultant solution was filtered under heating Ammonia water was added to the filtrate until the resultant solution by cooling with ice to precipitate a crystal The crystal was recovered by filtration by washing drying to obtain a crude product The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1)

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

Procedure: In a 2 liter-reaction vessel, 50.0 g (0.28 M) of p-hexylaniline, 54.8 g (0.56 M) of potassium thiocyanate and 400 ml of acetic acid were placed and cooled below 10° C. To the mixture, a solution of 45.0 g of bromine in 135 ml of acetic acid was added dropwise in 40 minutes below 10° C. under strong stirring, followed by reaction for 1.5 hours below 10° C. After the reaction, 500 ml of water was poured into the reaction mixture, followed by heating to dissolve the resultant precipitate. The resultant solution was filtered under heating. Ammonia water was added to the filtrate until the resultant solution became basic, followed by cooling with ice to precipitate a crystal. The crystal was recovered by filtration, followed by washing and drying to obtain a crude product. The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1) to obtain 33.0 g of 2-amino-6-hexylbenzothiazole (Yield: 49.9%). cooled below 10° C followed by reaction for 1.5 hours below 10° C was poured into the reaction mixture by heating The resultant solution was filtered under heating Ammonia water was added to the filtrate until the resultant solution by cooling with ice to precipitate a crystal The crystal was recovered by filtration by washing drying to obtain a crude product The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1)

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

Procedure: In a 2 liter-reaction vessel, 50.0 g (0.28M) of p-hexylaniline, 54.8 g (0.56M) of potassium thiocyanate and 400 ml of acetic acid were placed and cooled below 10° C. To the mixture, a solution of 45.0 g of bromine in 135 ml of acetic acid was added dropwise in 40 minutes below 10° C. under strong stirring, followed by reaction for 1.5 hours below 10° C. After the reaction, 500 ml of water was poured into the reaction mixture, followed by heating to dissolve the resultant precipitate. The resultant solution was filtered under heating. Ammonia water was added to the filtrate until the resultant solution became basic, followed by cooling with ice to precipitate a crystal. The crystal was recovered by filtration, followed by washing and drying to obtain a crude product. The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1) to obtain 33.0 g of 2-amino-6-hexylbenzothiazole (Yield: 49.9 %). cooled below 10° C followed by reaction for 1.5 hours below 10° C was poured into the reaction mixture by heating The resultant solution was filtered under heating Ammonia water was added to the filtrate until the resultant solution by cooling with ice to precipitate a crystal The crystal was recovered by filtration by washing drying to obtain a crude product The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1)

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