Morpholine → HCID 67508051, compound

Temperature

100 °C

To a flask containing 4-amino-2-chloro-5-iodobenzonitrile (1 g, 3.6 mmol) in DMSO (5.0 mL) was added morpholine (1.0 mL, 11.5 mmol) dropwise. Upon complete addition, the mixture was warmed to 100° C. After 40 h, the reaction mixture was cooled to rt, then an additional 2 mL of morpholine was added to the mixture. The reaction was re-heated to 100° C. and monitored with LC-MS. After 17 h, the reaction was cooled to rt, then 1 g of potassium carbonate was added in portions. The reaction was re-heated to 100° C. and monitored with LC-MS. After 13 days, the reaction was diluted with water then subsequently extracted five times with EtOAc. The organic extractions were then washed one time with brine and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-35% EtOAc in hexanes) to afford a pale brown solid as 4-amino-5-iodo-2-morpholinobenzonitrile. 1H NMR (500 MHz, CDCl3) δ ppm 7.80 (1H, m), 6.27 (1H, s), 4.57 (2H, br. s.), 3.92 (4H, m), 3.20 (4H, m). Mass Spectrum (pos.) m/e: 330.0 (M+H)+.

1. additionUpon complete addition
2. temperaturethe reaction mixture was cooled to rt
3. temperatureThe reaction was re-heated to 100° C.
4. waitAfter 17 h
5. temperaturethe reaction was cooled to rt
6. temperatureThe reaction was re-heated to 100° C.
7. waitAfter 13 days
8. extractionthen subsequently extracted five times with EtOAc
9. extractionThe organic extractions
10. washwere then washed one time with brine
11. dry with materialdried over anhydrous magnesium sulfate
12. filtrationAfter filtration and concentration
13. customthe residue was purified on silica gel (0-35% EtOAc in hexanes)

ORD record

ord-324811ca45754a949e9b024a9f8a7243

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940724B2