Practical and Efficient Chlorination of Deactivated Anilines and Anilides with NCS in 2-Propanol

Abstract

Deactivated anilines and anilides were efficiently monochlorinated with NCS in 2-propanol. The described method was applicable to a large scale synthesis.

Synthesis of Benzotriazine and Aryltriazene Derivatives Starting from 2‐Azidobenzonitrile Derivatives

“…The product was obtained after extraction with EtOAc (3 ϫ 20 mL) followed by evaporation which resulted in a yellow oil (0.92 g, 91 % 2-Azido-5-chlorobenzonitrile (4e): [20] This compound was prepared from 2-amino-5-chlorobenzonitrile (6e; [30] 2.85 g, 18.7 mmol) according to the procedure given for compound 4a. The product was obtained as a yellow solid (2.40 g, 72 %), m.p.…”

“…[28] The total yield of the desired product was (83 % 2-Amino-3,5-dimethylbenzonitrile (6d): [29] This compound was prepared from 2,4-dimethylaniline (9.8 g, 80.9 mmol) in two steps according to ref. [29] The product was obtained as a dark-brown oil (4.8 g, 41 % [30] This compound was prepared from 2-aminobenzonitrile (6a; 5.0 g, 42.4 mmol) and N-chlorosuccinimide (NCS; 5.93 g, 44.4 mmol) according to ref. [30] The product was obtained as a pale-yellow solid (4.3 g, 67 %), m.p.…”

“…[29] The product was obtained as a dark-brown oil (4.8 g, 41 % [30] This compound was prepared from 2-aminobenzonitrile (6a; 5.0 g, 42.4 mmol) and N-chlorosuccinimide (NCS; 5.93 g, 44.4 mmol) according to ref. [30] The product was obtained as a pale-yellow solid (4.3 g, 67 %), m.p. 95-96°C (ref.…”

Benzenesulfonamides with benzimidazole moieties as inhibitors of carbonic anhydrases I, II, VII, XII and XIII

“…1-(4-Amino-3-chlorophenyl)ethanone was synthesized by the chlorination of 1-(3-aminophenyl)-N ethanone with N-chlorosuccinimide in acetonitrile 25,26 . 2-Substituted benzimidazoles (b-i) were prepared from 1,2-benzenediamine and the appropriate carboxylic acids according to Phillips' procedure 27 .…”

Synthesis of 4-([18F]fluoromethyl)-2-chlorophenylisothiocyanate: A novel bifunctional 18F-labelling agent

“…In this context, the short-lived positron emitter fluorine-18 ( 18 F, t 1/2 = 109.7 min) is a particularly attractive radionuclide, thanks to its favourable nuclear and chemical properties. 18 F can be produced via several nuclear reactions at particle accelerators (cyclotrons) in relatively high quantities and high specific radioactivity. Its low positron energy of 0.64 MeV results in low radiation doses and short tissue range.…”