Chlorotrimethylsilane → HCID 1534791, compound

Temperature

100 °C

Into a 100-mL round-bottom flask, was placed a solution of 4-bromoaniline (1.71 g, 9.94 mmol), N′-formylformohydrazide (2.64 g, 30.0 mmol), and triethylamine (9.74 mL, 69.9 mmol, 7.00 equiv) in pyridine (40 mL). Chlorotrimethylsilane (19.2 mL, 151 mmol) was added drop-wise and the resulting solution was stirred for 18 h at 100° C., then cooled to room temperature. The resulting mixture was concentrated under reduced pressure and the residue was diluted with brine (50 mL) and extracted with ethyl acetate (6×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was washed with ether (30 mL) and the solids were collected by filtration to yield the title compound as a pink solid (1.6 g, 72%).

1. customInto a 100-mL round-bottom flask, was placed
2. temperaturecooled to room temperature
3. concentrationThe resulting mixture was concentrated under reduced pressure
4. additionthe residue was diluted with brine (50 mL)
5. extractionextracted with ethyl acetate (6×50 mL)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. washThe residue was washed with ether (30 mL)
10. filtrationthe solids were collected by filtration

ORD record

ord-a726db9da34e4193a3a4f682be866ada

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2