Ammonia → HCID 57825099, compound

A solution of iodine (2.92 g, 11.5 mmol) in ethyl acetate (50 mL) was added dropwise over 25 min to a mixture of 4-[1-(3-bromo-phenyl)-vinyl]-1-trifluoromethoxy-benzene (3.6 g, 10.5 mmol) and silver cyanate (1.88 g, 12.6 mmol) in acetonitrile (38 mL) and ethyl acetate (18 mL), cooled in an ice bath. After complete addition, the reaction suspension was stirred for another 15 min at room temperature when TLC indicated the complete conversion of starting material. The reaction mixture was filtered, and the filtrate concentrated to give a dark grey oil. 50 mL of aqueous ammonia (25%) was added to the oil, and the mixture was stirred and warmed to 60° C. for 4 hours. LC-MS at this point indicated complete conversion of the intermediate urea to the desired aminoxazoline. dichloromethane (40 mL) was added to the crude and the two phases were separated; organic layer was collected, dried over magnesium sulfate anhydrous, filtered and evaporated under reduced pressure. Crude was purified by silica gel chromatography eluting with dichloromethane to give 1.9 g of desired product as a colorless oil (45%)

1. temperaturecooled in an ice bath
2. additionAfter complete addition
3. filtrationThe reaction mixture was filtered
4. concentrationthe filtrate concentrated
5. customto give a dark grey oil
6. stirringthe mixture was stirred
7. temperaturewarmed to 60° C. for 4 hours
8. customthe two phases were separated
9. customorganic layer was collected
10. dry with materialdried over magnesium sulfate anhydrous
11. filtrationfiltered
12. customevaporated under reduced pressure
13. customCrude was purified by silica gel chromatography
14. washeluting with dichloromethane

ORD record

ord-4d8366b686934893862bd8206587fdf0

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989449B2