2-Methyl-6-nitrobenzoxazole

The synthetic route for 1 was outlined in Scheme 1, and the detailed procedures were presented as follows: (a) To a solution of 2-amino-5-nitrophenol (7.70g, 50.0mmol) and pyridine (3.96g, 50.0mmol) in dry xylene (150mL) at 0°C was added dropwise acetyl chloride (4.32g, 55.0mmol). The solution was stirred at ambient temperature for 2h. To above solution was added p-toluenesulfonic acid (1.72g, 10.0mmol), the solution was refluxed till no water was discharged. After cooling to room temperature, the solution was washed with water (100mL×3) and a saturated solution of NaCl (50.0mL), respectively. The organic solution was collected and dried over NaGeneral procedure: To a mixture of N-acyl or benzoy lderivative (6, 1 mmol) in water (5 mL) was added amberlyst-15 (10percent, w/w) and the mixture was irradiated with ultrasound (40 KHz) continuously at 90 °C till the completion of the reaction (monitored by TLC) as indicated in Table 4. The solid separated was filtered, washed with diethyl ether (2 x 5 mL), dried and treated with EtOAc (15 mL). After stirring for 10 min the mixture was filtered to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid obtained was purified by recrystallization (column chromatography in few cases) to afford the desired products 7, 8 or 9.

Molecular Weight:178.14
XLogP3:2
Hydrogen Bond Acceptor Count:4
Exact Mass:178.03784206
Monoisotopic Mass:178.03784206
Topological Polar Surface Area:71.8
Heavy Atom Count:13
Complexity:216
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes