Category: 622-24-2

622-24-2, Name is (2-Chloroethyl)benzene, 622-24-2, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

methyl 5-(phenethylamino)-2-(phenylsulfonamido)benzoate (13) To a round-bottom-flask under nitrogen methyl 5-amino-2-(phenylsulfonamido)benzoate 12 (184 mg, 0.6 mmol, 1.0 equiv.) and dry DMF (20 mL) were added. This was followed by addition of K2CO3 (691 mg, 3 mmol, 5.0 equiv.) and 1 -(2-chloroethyl)benzene (0.199 mL, 211 mg, 1.5 mmol, 2.5 equiv.) and the mixture was heated at 120 C for 16 hours. The reaction mixture was then allowed to cool down to room temperature and diluted with ice H20 (20 mL). The resulting mixture was extracted with Et^O (2 x 30 mL). All the organic extracts were combined, dried over NaS04 and concentrated. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=50:50) on silica gel to afford 13 (211 mg, 85%) as yellow oil. lH NMR (400 MHz, CDC13) delta 7.62-7.12 (m, 11H), 6.71-6.64 (m, 2H), 3.92-3.69 (m, 6H), 3.03-2.85 (m, 2H); 1 C NMR (100 MHz, CDC13) delta 166.57, 146.52, 139.75, 138.58, 133.08, 132.16, 131.83, 128.78, 128.64, 128.41, 127.73, 127.38, 126.31, 117.75, 117.00, 53.61, 52.04, 35.58.

Statistics shows that (2-Chloroethyl)benzene is playing an increasingly important role. we look forward to future research findings about 622-24-2.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 622-24-2, name is (2-Chloroethyl)benzene, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 622-24-2. 622-24-2

1-Chloro-2-phenylethane (57.0 mg, 0.41 mmol) and K2CO3 (298 mg, 2.16 mmol) were added to a solution of the secondary amine 3b (58.6 mg, 0.27 mmol) in acetonitrile (10 mL). The mixture was filled into a 10 mL-microwave pressure vial and irradiated with microwaves (program: standard; max. power 180 W; max. pressure 5 bar; temperature 140 C; time program: 5 min ramp time; 25 min hold time; 5 min cool off time). The mixture was filtered through Celite, washed with CH2Cl2, concentrated in vacuo and the residue was purified by fc (1 cm, petroleum ether/ethyl acetate 7:3, 5 mL, Rf = 0.22). Pale yellow oil, yield 40 mg (45%). C21H25NO2 (323.4). Anal. calcd. C 77.99 H 7.79 N 4.33 found C 77.73 H 7.85 N 4.24. MS (EI): m/z = 292 [M+ – OCH3], 232 [M+ – CH2Ph]. IR: (cm-1) = 2939 (nu C-H), 1076 (nu C-O), 752/698 (delta C-H monosubst. benzene). 1H NMR (CDCl3): delta (ppm) = 2.11-2.20 (m, 0.5H, CH2CH2N (cis or trans)), 2.29-2.46 (m, 1.5H, CH2CH2N (cis, trans)), 2.77-3.06 (m, 9H, N(CH2)2Ph (4H), CH2CH2NCH2 (4H), ArCH2CHOCH3 (1.5H; cis, trans)), 3.19-3.24 (m, 0.5H, ArCH2CHOCH3), 3.53/3.54 (2s, together 3H, OCH3 (cis, trans)), 4.80-4.85 (m, 1H, ArCH2CHOCH3), 7.03-7.08 (m, 1H, arom. H), 7.15-7.39 (m, 8H, arom. H). Ratio of diastereomers 52:48.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of (2-Chloroethyl)benzene.

Reference:
Article; Jasper, Annemarie; Schepmann, Dirk; Lehmkuhl, Kirstin; Vela, Jose Miguel; Buschmann, Helmut; Holenz, Joerg; Wuensch, Bernhard; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 327 – 336;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics