In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Trifluoromethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.
Synthetic Route of 830-43-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
To a solution of 27 (9.00 g, 19.0 mmol) in THF (130 mL) was added 1,1?-carbonyldiimidazole (6.15 g, 38.0 mmol) at r.t. and the solution was stirred at r.t. for 2 h. In another flask 4-(trifluoromethyl)benzenesulfonamide (6.40 g, 28.5 mmol) and DBU (4.00 mL, 26.6 mmol) were dissolved in THF (260 mL). To this solution was added the above solution containing the acyl imidazole reagent. After stirring for 4 h at the same temperature, EtOAc and aq NH4Cl were added. The resulting solution was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4), and filtered. The filtrate was concentrated in vacuo and the residue was purified roughly by flash column chromatography(SiO2; n-hexane-EtOAc, 4:1) to give a mixture of 53c and4-(trifluoromethyl)benzenesulfonamide as a yellow oil, which was used in the next step without further purification. The spectroscopic data for 53c were collected after purification by PTLC (SiO2; n-hexane-EtOAc, 3:1); [alpha]D27 -13.1 (c = 1.00, CHCl3).IR (film): 3105, 2952, 2931, 2857, 1710, 1508, 1322, 1231, 1175,1062, 835, 777 cm-1.1H NMR (400 MHz, CDCl3): delta = 11.02 (s, 1 H), 8.19 (d, J = 8.3 Hz, 1 H),7.76 (d, J = 8.3 Hz, 1 H), 6.82 (dd, J = 6.8, 2.8 Hz, 2 H), 6.74 (dd, J = 6.8,2.8 Hz, 2 H), 4.02 (dddd, J = 6.5, 6.5, 6.5, 3.2 Hz, 1 H), 3.80-3.70 (m, 5H), 2.73 (dd, J = 18.1, 10.9 Hz, 1 H), 2.68-2.63 (m, 1 H), 2.55-2.45 (m, 2H), 2.32 (ddd, J = 15.8, 8.0, 8.0 Hz, 1 H), 2.10 (ddd, J = 14.2, 10.1, 4.6 Hz,1 H), 2.00-1.81 (m, 2 H), 1.80-1.70 (m, 1 H), 1.62-1.45 (m, 3 H), 0.85(s, 9 H), 0.02 (s, 3 H), 0.00 (s, 3 H).13C NMR (100 MHz, CDCl3): delta = 212.9 (C), 165.9 (C), 153.8 (C), 152.8(C), 142.7 (C), 135.5 (C, q, J = 32.4 Hz), 129.0 (CH), 125.9 (CH, q, J = 3.8Hz), 122.8 (CF3, q, J = 271.7 Hz), 115.2 (CH), 114.7 (CH), 67.8 (CH2),64.3 (CH), 55.7 (CH3), 53.5 (C), 49.3 (C), 46.6 (CH2), 40.7 (CH), 33.6(CH2), 29.7 (CH), 29.2 (CH2), 26.9 (CH2), 26.8 (CH2), 25.7 (CH3), 17.9(C), -4.9 (CH3), -5.0 (CH3).HRMS (ESI+): m/z calcd for C33H41F3NO7SSiNa2: 726.2121; found:726.2147.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Trifluoromethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Ochi, Yuji; Yokoshima, Satoshi; Fukuyama, Tohru; Synthesis; vol. 49; 1; (2017); p. 96 – 114;,
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