N-Methoxy-N-methylacetamide → HCID 67516439, compound

Temperature

-78 °C

A 2M solution of LDA (35.2 mL, 70.3 mmol) in THF (176 mL) cooled to −78° C. was treated with slow addition of 4-bromo-N,N-diethyl-2-methylbenzamide (19 g, 70.3 mmol) in dry THF (176 mL). The reaction was allowed to stir at −78° C. for 1 hour before it was quenched with N-methoxy-N-methylacetamide (22.43 mL, 211 mmol) and allowed to slowly warm to room temp. The reaction was stirred overnight and then partitioned between 1N HCl (200 mL) and EtOAc (400 mL). The aqueous layer was further extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine (150 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was an oil out of which the product precipitated. The oil was decanted off and the solid was washed with hexanes and dried using a buchner funnel to afford 4-bromo-N,N-diethyl-2-(2-oxopropyl)benzamide: LC-MS: (M+H)+312.

1. temperatureto slowly warm to room temp
2. stirringThe reaction was stirred overnight
3. custompartitioned between 1N HCl (200 mL) and EtOAc (400 mL)
4. extractionThe aqueous layer was further extracted with EtOAc (2×150 mL)
5. washThe combined organic layers were washed with brine (150 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customprecipitated
10. customThe oil was decanted off
11. washthe solid was washed with hexanes
12. customdried

ORD record

ord-933a99c102704df7a8d4401d7e896d58

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206199B2