Hydrochloric Acid → HCID 86715962, compound

Participants

Reaction Steps

N-(3-Aminophenyl)-2-(diethylamino)acetamide 5 (0.52 g, 2.35 mmol) was dissolved in THF (6 ml), and cooled in an ice bath. The resulting stirred mixture was treated sequentially with concentrated aqueous HCl (1.08 ml, 12.92 mmol), then with tBuONO (0.61 g, 5.87 mmol). The reaction was stirred in an ice bath for 1.5 hours and after that time NaN3 (0.46 g, 7.05 mmol) was added, followed by careful addition of water, until the reaction ceased to effervesse. The reaction was allowed to warm to room temperature and stirred overnight. The mixture was carefully neutralised with saturated aqueous NaHCO3 solution and THF was evaporated in vacuo. The aqueous solution was extracted three times with EtOAc (75 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo, to give N-(3-azidophenyl)-2-(diethylamino)acetamide 6 as a dark brown oil (0.56 g, 85%) without requiring any further purification; Rf 0.24 [10% MeOH in DCM]; IR (film): 3279.67, 2934.63, 2110.57, 1687.86, 1515.73 cm−1; δH (CDCl3, 400 MHz) 9.43 (1H, s, NH), 7.41 (1H, m, ArH), 7.30-7.23 (2H, m, 2×ArH), 6.76 (1H, td, J1=8.0, J2=2.0 Hz, ArH), 3.13 (2H, s, CH2), 2.64 (4H, m, 2×CH2), 1.08 (6H, m, 2×CH3); δC (CDCl3, 100 MHz) 170.25 (C═O), 140.95 (Ar—C), 139.18 (Ar—C), 130.14 (Ar—CH), 115.60 (Ar—CH), 114.48 (Ar—CH), 109.96 (Ar—CH), 58.11 (CH2), 48.92 (2×CH2), 12.40 (2×CH3); LC-MS (5 min) m/z 248.49 [C12H17N5O+H]+ (25), 220.07 [(C12H17N5O+H)-28]+ (40) Rt 2.05 min; HRMS m/z calc. C12H18N5O [M+H]+248.1506. found [M+H]+ 247.1498.

Provenance & Evidence