* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With potassium hydroxide; benzyltriethylammonium bromide In water; xylene at 115 - 120℃; for 3 h;
Example 5; n-Hexadecyl-3-amino-4-chlorobenzoate: A mixture of 16.3 g (0.132 moles) 45percent potassium hydroxide solution, 21.5 g (0.125 moles) of 3-amino-4-chlorobenzoic acid, 100 g of xylene, 40/3 g (0.132 moles) of 1-bromohexadecane and 4.5 g of benzyltriethylammonium bromide (10 mole percent) were heated to reflux and water was removed by means of a Dean Stark trap. After 3 hr at reflux (115-120° C.) the reaction was judged complete by tic. The reaction was cooled to 90° C. and washed with water to remove salts. The solvent was removed on a roto-vap and the residue was crystallized from heptane to give 40.7 g (83percent yield) of a solid judged to be pure by nmr and by tic.
99.6 %Spectr.
With potassium hydroxide; tetrabutyl phosphonium bromide In water; 4-methyl-2-pentanone at 115 - 120℃; for 5 h;
Example 3; n-Hexadecyl-3-amino-4-chlorobenzoate: A mixture of 32.7 g (0.264 moles) 45percent potassium hydroxide solution, 43 g (0.25moles) of 3-amino-4-chlorobenzoic acid, 200 g of methyl isobutyl ketone, 80.6g (0.264 moles) of 1-bromohexadecane and 4.4 g of tetrabutylphosphonium bromide (5 mole percent) were heated to reflux and water was removed by means of a Dean Stark trap. After 5 hr at reflux (115-120° C.) the reaction was judged complete by tic. The reaction was cooled to 90° C. and washed with water to remove salts. The solvent was removed on a roto-vap and the residue was crystallized from heptane to give 93.4 g (95percent yield) of a solid whose nmr weight percent assay was 99.6percent.
With potassium hydroxide; benzyltriethylammonium bromide; In water; xylene; at 115 - 120℃; for 3h;Product distribution / selectivity;
Example 5; n-Hexadecyl-3-amino-4-chlorobenzoate: A mixture of 16.3 g (0.132 moles) 45% potassium hydroxide solution, 21.5 g (0.125 moles) of <strong>[2840-28-0]3-amino-4-chlorobenzoic acid</strong>, 100 g of xylene, 40/3 g (0.132 moles) of 1-bromohexadecane and 4.5 g of benzyltriethylammonium bromide (10 mole percent) were heated to reflux and water was removed by means of a Dean Stark trap. After 3 hr at reflux (115-120 C.) the reaction was judged complete by tic. The reaction was cooled to 90 C. and washed with water to remove salts. The solvent was removed on a roto-vap and the residue was crystallized from heptane to give 40.7 g (83% yield) of a solid judged to be pure by nmr and by tic.
99.6%Spectr.
With potassium hydroxide; tetrabutyl phosphonium bromide; In water; 4-methyl-2-pentanone; at 115 - 120℃; for 5h;Product distribution / selectivity;
Example 3; n-Hexadecyl-3-amino-4-chlorobenzoate: A mixture of 32.7 g (0.264 moles) 45% potassium hydroxide solution, 43 g (0.25moles) of <strong>[2840-28-0]3-amino-4-chlorobenzoic acid</strong>, 200 g of methyl isobutyl ketone, 80.6g (0.264 moles) of 1-bromohexadecane and 4.4 g of tetrabutylphosphonium bromide (5 mole percent) were heated to reflux and water was removed by means of a Dean Stark trap. After 5 hr at reflux (115-120 C.) the reaction was judged complete by tic. The reaction was cooled to 90 C. and washed with water to remove salts. The solvent was removed on a roto-vap and the residue was crystallized from heptane to give 93.4 g (95% yield) of a solid whose nmr weight percent assay was 99.6%.
equipped with a thermometer, a water separator,156 g (0.91 mol) of <strong>[2840-28-0]3-amino-4-chlorobenzoic acid</strong>, 264 g (1.09 mol) of n-hexadecanol, 45 g of toluene, and 182 g of xylene were respectively added to a three-necked flask of a stir bar, and the mixture was heated to 50 C with stirring, and kept at a constant temperature for 1 h. After n-hexadecanol was completely dissolved, 18.8 g (0.109 mol) of p-toluenesulfonic acid was added.Heating was continued at a reflux temperature of 152 to 164 C for 10 h to stop the reaction.Add 1500 mL of methanol, cool to 20 C, crystallization time 5 h, filter,After the filter cake was dried, 292 g of a crude product was obtained, and 1500 mL of the first filtrate was collected.Add 1500 mL of methanol to the crude product, heat to 70 C to be completely dissolved, and cool to 10 C.Recrystallization time 8h, filtration, drying the filter cake to obtain 284g finished productHexadecyl 3-amino-4-chlorobenzoate, yield 78.81%,A second filtrate of 1500 mL was collected. HPLC test analysisThe purity of hexadecyl 3-amino-4-chlorobenzoate was 98.50%.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
