Avance av 400 mhz

FDMA was synthesized according to the reaction route shown in Scheme 1. Firstly, a urethane precursor was synthesized through the reaction between (22.23 g, 0.10 mol) IPDI (1) and (23.11 g, 0.05 mol) PFDOL (2) at 45 °C. In this reaction, THF and a few droplets of DBTDL were used as the solvent and catalyst, respectively. When the -NCO groups content reached half of the initial content (determined by dibutyl amine titration) to form (3), 13.01 g (0.10 mol) of HEMA (4) were added into the reactor and the reaction was continued under 45 °C. The reaction was stopped until the infrared absorbance peak of the -NCO group (2270 cm⁻¹) disappeared in the FT-IR (Fourier Transform Infrared; Vector33, Bruker Co., Bremen, Germany) spectra of the samples taken from the reaction medium every 1 h. After removing the THF by distillation under vacuum, the product FDMA (5) was obtained as a colorless viscose liquid. The structure of FDMA was investigated by FT-IR and ¹H-NMR (Proton Nuclear Magnetic Resonance Instrument; Avance AV 400 MHz, Bruker Co., Fällanden, Switzerland) spectra.

Chemicals were purchased from Sigma Aldrich (St. Louis, MO, USA) and Alfa Aesar (Ward Hill, MA, USA). Melting points were taken on Griffin and George melting point apparatus using the open capillary tube method and were reported as uncorrected. Infrared spectra were recorded in KBr on a Jasco-320-A spectrophotometer. ¹H-NMR signals were recorded on AVANCE AV-300 MHz, AVANCE AV-400 MHz, or AVANCE AV-500 MHz while ¹³C-NMR spectra were taken on a Bruker AVANCE AV-75 MHz, AVANCE AV-100 MHz and AVANCE AV-125 MHz spectrometer. EIMS signals were recorded on JEOL MS 600H-1 spectrometer. 5-[2-(4-Chlorophenoxy)propan-2-yl]-1,3,4-oxadiazol-2-thiol 1 [29 ] and aromatic N-substituted-2-bromoacetamides (2a–2i) were synthesized by previously reported methods with slight modifications [12 ].