3‐Oxo‐2‐tosyl‐2,3‐dihydro‐1 H ‐1λ ₃ ‐benzo[ d ][1,2]iodazol‐1‐yl acetate (GenOx‐PJ)

Encyclopedia of Reagents for Organic Synthesis, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 2

Published: April 18, 2024

image [2243393‐44‐2] C 16 H 14 INO 5 S (MW 459.26) InChI = 1S/C16H14INO5S/c1‐11‐7‐9‐13(10‐8‐11)24(21,22)18‐16(20)14‐5‐3‐4‐6‐15(14)17(18)23‐12(2)19/h3‐10H,1‐2H3 InChiKey RQDQCGBTXDPXTH‐UHFFFAOYSA‐N (decarboxylation hypervalent iodine reagent) Physical Data : mp: 160 °C. Solubility soluble in dichloromethane, 1,2‐dichloroethane, acetone, and acetic acid. Insoluble diethyl ether, hexanes, isopropyl acetate, acetonitrile, methanol, water. Form Supplied white powder, commercially available. Analysis of Reagent Purity 1 NMR (400 MHz, d 6 ‐DMSO, δ): 8.02−7.95 (m, 2 ), 7.95–7.89 7.86 (dd, J 8.8, 0.9 Hz, 7.80–7.71 7.44 (d, 8.1 2.38 (s, 3 2.26 ) ppm. 13 C{1 } (101 174.1, 162.4, 144.5, 136.8, 136.0, 132.3, 131.4, 131.2, 129.7, 128.8, 127.9, 118.0, 21.1, 20.2 Preparative Method three‐step synthesis from 2‐iodobenzoic acid (eq 1). Step 1. Synthesis 2‐iodo‐ N ‐tosylbenzamide. Thionyl chloride (3.53 mL, 48.4 mmol) followed by DMF (0.20 2.6 was added to (10.0 g, 40.3 CH Cl (200 mL). The mixture stirred for h at room temperature. solvent evaporated, the residue dissolved toluene (32 mL), a solution 4‐toluenesulfonamide (6.90 mmol), triethylamine (14.0 101 DMAP (0.250 2.02 EtOAc (80 heated 60 °C, then cooled temperature, quenched with M HCl (50 extracted (3 × 50 combined organic extracts were washed brine dried over MgSO 4 . drying agent filtered off, evaporated. purified column chromatography (silica, affording ‐tosylbenzamide (15.8 39.5 mmol, 98%) as colorless oil. 2. Caution: For safety reasons, reaction carried out behind an antiblast shield. mCPBA (77% pure; 8.85 39.6 Ac O (160 1.68 mol) AcOH (158 resulting 48 80 Thereafter, ether (150 mL) added. desired compound (7.13 15.5 39%) crystallized 0 °C collected filtration. Purification recrystallization ether. Handling, Storage, Precautions store under inert atmosphere −20 dark. Might be shock sensitive.

Language: Английский

Preparation of benziodazole-triflate and its application as both 2-iodobenzamido- and triflate-transfer reagents

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110338 - 110338

Published: Aug. 1, 2024

Language: Английский