Ammonia → HCID 67325699, compound

Thionyl chloride (0.570 mL, 7.81 mmol) was added to a solution of 2-bromo-3-methylbenzoic acid (1.60 g, 7.44 mmol) and DMF (0.058 mL, 0.744 mmol) in DCM (50 mL) at 0° C. The reaction mixture was allowed to warm to RT and stirred for 1 hr and then cooled to 0° C. before ammonia 2N i-PrOH (18.60 mL, 37.2 mmol) was added. The resulting cloudy solution was stirred for 30 min. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with 10% sodium carbonate, saturated ammonium chloride, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material as a white solid. The solid was dissolved in EtOH (30 mL) and divided evenly into 2×20 mL microwave vials. 1-Chloro-2-propanone (0.574 mL, 7.44 mmol) was added into each vial and the reaction mixture was stirred and heated in a microwave reactor at 150° C. for 2 h. The reactions were concentrated and the crude material was purified by silica gel chromatography to provide 2-(2-bromo-3-methylphenyl)-4-methyloxazole.

1. additionwas added
2. stirringThe resulting cloudy solution was stirred for 30 min
3. extractionextracted with EtOAc
4. washThe combined organic extracts were washed with 10% sodium carbonate, saturated ammonium chloride, saturated sodium chloride
5. dry with materialdried over sodium sulfate
6. filtrationThe solution was filtered
7. concentrationconcentrated in vacuo
8. customto give the crude material as a white solid
9. stirringwas stirred
10. temperatureheated in a microwave reactor at 150° C. for 2 h
11. concentrationThe reactions were concentrated
12. customthe crude material was purified by silica gel chromatography

ORD record

ord-ca5c8f750fba4324899b601b7b978f64

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735384B2