106. MS (EI) m/z 149 (M+). 1-Azido-4-methylbenzene (Az3). Yield 41 ; yellow oil; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 7.22 (2H, d, J = 7.5 Hz), 7.01 (2H, d, J = eight.five Hz), 2.28 (3H, s). FTIR (neat, cm21) 2121. MS (EI) m/z 133 (M+). 1-Azido-4-fluorobenzene (Az4). Yield 50 ; yellow oil; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 7.31?.22 (2H, m), 7.21?7.13 (2H, m). FTIR (neat, cm21) 2106. MS (EI) m/z 137 (M+). 1-Azido-4-bromobenzene (Az5). Yield 54 ; yellow oil; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 7.60 (1H, d, J = 9.0 Hz), 7.11 (2H, d, J = 9.0 Hz). FTIR (neat, cm21) 2121. MS (EI) m/z 197 (M+), 199 (M++2). 4-Azidoaniline (Az7). Yield 37 ; red strong; 1H NMR (DMSO-d6, 500 MHz, d, ppm) six.77 (2H, d, J = 8.7 Hz), 6.59 (2H, d, J = eight.8 Hz), five.13 (2H, s); FTIR (neat, cm21) 2106. MS (EI) m/z 134 (M+). 1-Azido-3,4-dimethylbenzene (Az11). Yield 95 ; yellow oil; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 7.18 (1H, d, J = 8.0 Hz), 6.92 (1H, s), 6.84 (1H, d, J = eight.0 Hz). FTIR (neat, cm21) 2102. MS (EI) m/z 147 (M+).1-Azido-4-iodobenzene (Az6). To a option of 4-iodoaniline (11, 1.07 g, four.87 mmol) in TFA (ten mL) was added a answer of NaNO2 (1.45 g, 21.0 mmol) in water (10 mL) at 0uC. The mixture was stirred at 0uC for ten min and also a option of NaN3 (3.two g, 49.2 mmol) in water (10 mL) was added. The reaction mixture was diluted with AcOEt, washed with water and brine, and dried over Na2SO4. Filtration and concentration in vacuo, and recrystallization from AcOEt gave 1.07 g (90 ) of Az6 as a black solid. 1H NMR (DMSO-d6, 500 MHz, d, ppm) 7.73 (2H, d, J = 8.5 Hz), six.95 (2H, d, J = 8.5 Hz). FTIR (neat, cm21) 2096. MS (EI) m/z 245 (M+). Compounds Az8 z10 and Az12 have been ready from an proper aniline (11?five) utilizing the procedure described for Az6. 4-Azidonitrobenzene (Az8). Yield 80 ; yellow solid; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 8.24 (2H, d, J = 9.0 Hz), 7.35 (2H, d, J = 9.0 Hz). FTIR (neat, cm21) 2121. MS (EI) m/z 164 (M+). 4-Azidophenol (Az9). Yield 18 ; black strong; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 9.55 (1H, s), 6.91 (2H, d, J = 9.0 Hz), six.78 (2H, d, J = 9.0 Hz); FTIR (CHCl3, cm21) 2114; MS (EI) m/z 135 (M+). 2-Azidophenylbenzene (Az10). Yield 87 ; yellow oil; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 7.6-Bromoquinoline-3-carbaldehyde supplier 50?.945459-80-3 Chemscene 40 (5H, m), 7.PMID:33518554 37 (3H, t, J = eight.0 Hz), (1H, t, J = 7.3 Hz). FTIR (CHCl3, cm21) 2125. MS (EI) m/z 167 (M+ 2). 1-Azidonaphthalene (Az12). Yield 43 ; brown oil; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 7.94 (1H, d, J = eight.0 Hz), 7.87 (1H, d, J = 8.0 Hz), 7.68 (1H, d, J = eight.0 Hz), 7.53?.44 (3H, m), 7.36 (1H, d, J = 7.5 Hz). FTIR (neat, cm21) 2110. MS (EI) m/ z 169 (M+). 2-Azido-N-(4-fluorophenyl)acetamide (Az13). To a answer of 0.5 M NaN3 (16 mmol) in DMSO (32 mL) was added 2chloro-N-(4-fluorophenyl)acetamide (16, 1.0 g, five.3 mmol), plus the mixture was stirred at space temperature for 24 h. The reaction mixture was diluted with AcOEt, washed with water and brine, and dried over Na2SO4. Filtration, concentration in vacuo, and purification by silica gel flash column chromatography (AcOEt/nhexane = 1/2) gave 1.0 g (97 ) of AZ13 as a brown strong. 1H NMR (DMSO-d6,, 500 MHz, d, ppm) 10.2 (1H, s), 7.60?.55 (2H, m), 7.19?.12 (2H, m), 4.03 (2H, s). FTIR (neat, cm21) 2102. MS (EI) m/z 194 (M+). Compound Az14 was ready from 2-chloro-N-(2,6-dimethylphenyl)acetamide 17 and NaN3 using the procedure described for Az13. 2-Azido-N-(two,6-dimethylphenyl)acetamide (Az14). Yield 64 ; white solid; 1H NMR (DMSO-d6, 500 MHz, d, ppm) 9.51 (1H, s), 7.09 (3H, m), four.09 (2H, s), 2.14 (6H, s). FTIR (neat, cm21) 2094.