Potassium Carbonate → HCID 178497363, compound

HRID 1487819Notes

Reaction equation

Br[CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH3:16])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])=O.Cl.[C:19](=[NH:22])([NH2:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][C:19]1[NH:21][C:3]([C:5]2[C:6]([CH3:16])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=2)[C:10]([O:12][CH3:13])=[O:11])=[C:2]([CH3:17])[N:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Into a round-bottom flask, was placed a solution of methyl 5-(2-bromopropanoyl)-2,4-dimethylbenzoate (compound 1.6, 400 mg, 1.34 mmol) in acetonitrile (30 mL). Acetimidamide hydrochloride (260 mg, 2.75 mmol) and potassium carbonate (550 mg, 3.99 mmol) were added and the resulting mixture was stirred at 80° C. for 15 h. After cooling to room temperature, the mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate (50 mL) and washed with brine (2×25 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1) to ethyl acetate as the eluent to yield the title compound as a yellow oil (0.20 g, 58%).

Workup

customInto a round-bottom flask, was placed
temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated under reduced pressure
additionthe residue was diluted with ethyl acetate (50 mL)
washwashed with brine (2×25 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1) to ethyl acetate as the eluent

Sources & evidence

ORD record: ord-552a72d8e85c447b9021220b8bb1cdb3
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

Loading…