Acetone → 4-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamide

Temperature

80 °C

N-methyl-2-fluoro-4-aminobenzamide 4a (1.68 g, 10 mmol) was added a TMS-CN (4.93 g 50 mmol) solution in acetone (30 mL). The reaction mixture was stirred at 80° C. for 12 h, then concentrated in vacuo. The residue was diluted with water (50 mL). The suspension was extracted with ethyl acetate (3×30 mL). Combined organic layers were washed with brine (3×50 mL), dried (MgSO4) and concentrated in vacuo to dryness. The resulting residue was triturated with a mixed solvent of hexanes and ethylether (20 mL-20 mL). The solid was collected by filtration, affording the title compound 6b (1.8 g, 79% yield). MS (ES-API Negative): 234 (M−H)−.

1. concentrationconcentrated in vacuo
2. additionThe residue was diluted with water (50 mL)
3. extractionThe suspension was extracted with ethyl acetate (3×30 mL)
4. washCombined organic layers were washed with brine (3×50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo to dryness
7. customThe resulting residue was triturated with a mixed solvent of hexanes and ethylether (20 mL-20 mL)
8. filtrationThe solid was collected by filtration

ORD record

ord-b82a05253fef413e8b0830e4cfbf3c95

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809550B2