Supplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes
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1 Supplementary Material onic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes Mahboobe Nouzarian 1, Rahman Hosseinzadeh 1,*, and Hamid Golchoubian 2 1 Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, ran 2 Department of norganic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, ran Corresponding Author r.hosseinzadeh@umz.ac.ir Corresponding Author Tel. & Fax: List of contents Page 1. General nformation S2 2. Experimental Procedures and Characterization Data S2-S General procedure for preparation of hexamethylene S2 bis(n-methylimidazolium) bis(dichloroiodate)(hmbmdcd) 2.2. General procedure for iodination of aromatic and S3 heteroaromatic amines 2.3. General procedure for iodination of terminal alkynes S Recovery of hexamethylene bis(n-methylimidazoilum) S4 bis(dichloroiodate) (HMBMBDC) H NMR and 13 C NMR spectra of some products S4-S6 3. Reference S6 S1
2 1. General nformation Materials were purchased from Fluka and Merck Chemical Companies. 1 H and 13 C NMR spectra were obtained on a Bruker Avance instrument at 400 and 100 MHz, respectively using CDCl 3, D 2 O and DMSO as solvents. Melting points were determined on an Electro Thermal All the products were characterized by 1 H NMR data, and some of the products were characterized by GC analyses. GC analyses were performed on a Perkin Elmer 8500 instrument using a Capillary column 30M with a FD detector under helium as carrier gas. GC parameters were quantified by the authentic product samples prior to the analysis. Elemental analyses were performed on a LECO 600 CHN elemental analyzer. odine percentage was determined by iodometric titration. [1] 2. Experimental Procedures and Characterization Data 2.1. General procedure for preparation of hexamethylene bis(nmethylimidazolium) bis(dichloroiodate) (HMBMBDC) (4a) Method 1. A mixture of N-methylimidazole (1a) (33.00 mmol, 2.71 g) and 1,6- dichlorohexane (2a) (15.00 mmol, 2.33 g) was stirred in DMF (10 ml) at 100 C for 4 h. After cooling the mixture, the hygroscopic white solid was immediately filtered, washed with diethyl ether (40 ml), and dried under vacuum to give hexamethylene bis(nmethylimidazolium) dichloride (HMBMDC) (3a) (3.30 g, 69%); mp C; 1 H NMR (D 2 O) δ: 8.61 (s, 2 H), 7.37 (s, 2 H), 7.33 (s, 2 H), 4.09 (t, J = 7.0 Hz, 4 H), 3.79 (s, 6 H), 1.77 (br quin, 4 H), 1.24 (br quin, 4 H); 13 C NMR (D 2 O) δ: , , , 49.36, 35.66, 29.02, Then HMBMDC (3a) (10.30 mmol, 3.30 g) was dissolved in H 2 O (20 ml) and was slowly added to an aqueous solution of NaCl 2 that was beforehand prepared. [2] The mixture was cooled to 0 C and the yellow-orange solid formed was collected by S2
3 filtration, washed first with a small quantity of H 2 O (10 ml) and then with Et 2 O (30 ml) and dried under vacuum to give HMBMBDC (4a) (5.0 g, 76%); mp C; 1 H NMR (DMSO- d 6 ) δ: 9.08 (s, 2 H), 7.74 (pseudo t, J = 1.6 Hz, 2 H), 7.70 (pseudo t, J = 1.6 Hz, 2 H), 4.14 (t, J = 7.2 Hz, 4 H), 3.85 (s, 6 H), 1.78 (br quin, 4 H), 1.27 (br quin, 4 H). 13 C NMR (DMSO- d 6 ) δ: 136.9, , , 49.16, 36.26, 29.61, Anal calcd for C 14 H 24 Cl 4 2 N 4 : C 24.73, H 4.15, N 8.24, found: C 24.63, H 3.90, N 8.13, Method 2. Following the typical procedure for 3a, the mixture of Cl (20.60 mmol, 3.34 g) in CH 2 Cl 2 (2 ml) was added to an aqueous solution of HMBMBDC (3a) (10.30 mmol, 3.30 g) in 0 C. The yellow-orange solid formed was collected by filtration, washed with Et 2 O (50 ml) and dried under vacuum to give HMBMBDC (4a) (4.9 g, 74%) General procedure for iodination of aromatic and heteroaromatic amines Aromatic amines (1.00 mmol) was treated with hexamethylene bis(nmethyimidazolium) bis(dichloroiodate) (4a) (0.70 mmol) in the presence of CaCO 3 (2.00 mmol) in a 25-mL round-bottomed flask equipped with a magnetic stirring bar at 30 C for the time specified in Table 1. After disappearance of the starting material as monitored by GC, the reaction mixture was quenched with water (20 ml) and was extracted with Et 2 O (40 ml) (Step 1). The organic layer was washed with aqueous NaHSO 3 (5%, 20 ml), dried over Na 2 SO 4 and evaporated in vacuum. The crude product was passed through a short column of silica gel and was recrystallized from CH 3 OH:H 2 O (2:1) to afford corresponding products shown in Table 1. All products were identified by comparing melting point and 1 H NMR with those of authentic samples reported in the literature General procedure for iodination of terminal alkynes To a solution of alkyne (0.50 mmol), DBU (0.50 mmol) in THF (2 ml) was added HMBMBDC (4a) (0.35 mmol) and stirred at room temperature for the time specified in S3
4 Table 3. The progress of the reaction was monitored by TLC and the reaction mixture was quenched with aqueous NaHSO 3 (5%, 20 ml) and was extracted with Et 2 O (40 ml). The organic layer was dried over Na 2 SO 4 and the resultant solution was evaporated under reduced pressure. The crude product was purified by preparative thin-layer chromatography. All products were identified by comparing melting point and 1 H and 13 C NMR with those of authentic samples reported in the literature Recovery of hexamethylene bis(n-methylimidazoilum) bis(dichloroiodate) (HMBMBDC) (4a) To a separated aqueous layer in step 1 was added a solution of NaCl 2 that was beforehand preparaed. [2] The reaction was immediately followed by formation of a yellow precipitate, which was then filtered, washed with Et 2 O and dried under vacuum to give HMBMBDC (4a) (67%). The yellow solid obtained was identical in all aspect with the parent HMBMBDC. This procedure was repeated three times for iodination of aniline, and the yield of the product was nearly the same H NMR and 13 C NMR spectra of some products are given below: N NH 2 2-Amino-5-iodopyridine (Table 1, Entry 7). 1 H NMR (CDCl 3 ): δ (ppm) = 8.24 (dd, J = 2.4, 0.5 Hz, 1 H), 7.66 (dd, J = 8.7, 2.4 Hz, 1 H), 6.39 (dd, J = 8.7, 0.5 Hz, 1 H), 4.40 (br s, 2 H). NH 2 N S 2-Amino-5-iodothiazole (Table 1, Entry 8). 1 H NMR (CDCl 3 ): δ (ppm) = 7.12 (s, 1 H), 4.98 (br s, 2 H). 13 CNMR : δ (ppm) = , , S4
5 CH 3 N H 2-odo-3-methyl indole (Table 1, Entry 12). 1 H NMR (CDCl 3 ): δ (ppm) = 7.89 (br s, 1 H), (m, 1 H), (m, 1 H), (m, 1 H), (m, 1 H), 2.28 (s, 3 H). Br 1-Bromo-2-(2-iodoethynyl) benzene (Table 3, Entry 3). 1 H NMR (CDCl 3 ): δ (ppm) = 7.59 (dd, J = 8.0, 1.2 Hz), 7.49 (dd, J = 7.8,1.8 Hz, 1 H), 7.28 (td, J = 15.0, 1.6 Hz, 1 H), 7.18 (td, J = 15.0, 1.6 Hz, 1 H). 13 CNMR: δ (ppm) = 11.93, 92.64, , , , , , MeO 2-(2-odoethynyl)-6-methoxynaphthalene (Table 3, Entry 6). 1 H NMR (CDCl 3 ): δ (ppm) = 7.91 (br s, 1 H), 7.69 (t, J = 8.6 Hz, 2 H), 7.46 (dd, J = 8.6, 1.6 Hz, 1 H), 7.18 (dd, J = 8.6, 2.4 Hz, 1 H), 7.12 (d, 2.4 Hz, 1 H), 3.94 (s, 3 H). 13 CNMR: δ (ppm) = , , , , , , , , , , 94.61, 55.38, (2-(4-(2-odoethynyl)phenyl)ethynyl)benzene (Table 3, Entry 8). 1 H NMR (CDCl 3 ): δ (ppm) = (m, 2 H), 7.47 (dd, J = 8.4 Hz, 4 H), (m, 3 H). 13 CNMR: δ (ppm) = , , , , , , , , 93.84, 91.64, 88.84, S5
6 CH 3 CH 2 CH 2 CH 2 C 1-odohex-1-yne (Table 3, Entry 9). 1 H NMR (CDCl 3 ): δ (ppm) = 2.38 (t, J = 7.0 Hz, 2 H), 1.52 (m, 2 H), 1.43 (m, 2 H), 0.93 (t, J = 7.4 Hz, 3 H). 13 CNMR: δ (ppm) = 94.80, 30.55, 21.87, 20.51, 13.56, Reference: 1. Skoog, D. A.; West, D. M.; Holler, F. J. Fundamentals of Analytical Chemistry, 5th ed.; Saunders College Publishing, Kosynkin, D. V.; Tour, J. M. Benzyltriethylammonium dichloroiodate/sodium bicarbonate combination as an inexpensive, environmentally friendly, and mild iodinating reagent for anilines. Org. Lett. 2001, 3, S6
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