2-(CHLOROMETHYL)-1,3-BENZOXAZOLE

B. To a stirred suspension of 2-aminophenol (365 mg, 3.35 mmol) in dichloromethane (7 mL) at 0To a solution of 2-aminophenol (3.76 g, 34.5 mmol) in methylene chloride at 0 °C was added ethyl chloroacetimidate hydrochloride (7.98 g, 50.5 mmol). After 85 min, the reaction mixture was allowed to warm to room temperature, while beingstirred overnight. The mixture was filtered over diatomite and concentrated to oil under reducedpressure. The resulting residue was purified by column chromatography on silica gel (petroleumether/acetone, 10:1 v:v) to obtain compound 3 as a white solid (5.00 g, 86.5percent). m.p., 152–154 °C;MS (+ESI) m/z 168.05 [M + H]+In a solution of 2-aminophenol (0.50 g, 4.6 mmol) dissolved inchlorobenzene (5 mL), 2-chloroacetyl chloride (0.52 g, 4.6 mmol) and pyridine (0.02 mL) were added.The mixture was stirred at room temperature for 2 h; then p-toluene sulfonic acid (0.08 g, 0.46 mmol)was added. The mixture was heated at reflux for 8 h and then cooled to room temperature. The solventwas removed under reduced pressure, and the resulting residue was dissolved in ethyl acetate (30 mL).The solution was washed with water and brine, dried over Na2SO4, and concentrated in vacuo.The residue was puri®ed by chromatography on silica gel (petroleum ether:ethyl acetate = 10:1) to give13g (0.70 g, 90.2percent) as a yellow oil.This compound was synthesized according to the previously described procedure.5 To a solution of 2-aminophenol (0.50 g, 4.58 mmol, 1.0 equiv.) in xylene (20 mL), chloroacetyl chloride (0.56 mL, 6.87 mmol, 1.5 equiv.) was added under argon, followed by drop-wise addition of Et3N (0.70 mL, 5.04 mmol, 1.1 equiv.). The reaction mixture was initially stirred for 2 h at room temperature and then overnight at 145 °C. A saturated aqueous solution of NH4Cl (50 mL) was added to the reaction mixture, and the biphasic system was transferred to a separating funnel. The mixture was extracted with EtOAc (3× 20 mL), and the combined organic phases were washed with saturated brine solution (50 mL), dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by short flash column chromatography using EtOAc/n-hex = 1/4 as eluent, to obtain 0.65 g of the compound. Yield: 85percent; transparent yellow oil (lit.5 colorless oil); 1H NMR (400 MHz, CDCl3): δ 4.76 (s, 2H, CH2), 7.35–7.42 (m, 2H, 2 × Ar-H), 7.55–7.57 (m, 1H, Ar-H), 7.74–7.76 (m, 1H, Ar-H).General procedure: 2-Methylquinolines 1(2 mmol), TBAI (2 mmol), urea (2 mmol), and 1, 2-dichloroethane (10 mL) weremixed in a microwave tube. The reaction mixture was stirred at 110 °C for 30 min under microwave irradiation using a CEM Discover microwave reactor(the highest power: 150 W; run time: 5 min; hold time: 30 min; temperature:110 °C). The resulting reaction mixture was concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel using hexane/EtOAc as eluent.

Molecular Weight:167.59
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:167.0137915
Monoisotopic Mass:167.0137915
Topological Polar Surface Area:26
Heavy Atom Count:11
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes