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

Temperature

-78 °C

A 2 M solution of lithium diisoproyl amine (35 ml, 70 mmol) in THF (180 mL) cooled to −78° C. was treated with slow addition of 4-bromo-N,N-diethyl-2-methylbenzamide (19 g, 70 mmol) in dry THF (180 mL). The reaction was allowed to stir at −78° C. for 1 hour before it was quenched with N-methoxy-N-methylacetamide (22 mL, 210 mmol) and allowed to slowly warm to room temperature. The reaction was stirred overnight and then partitioned between 1 N 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 orange/brown oil out of which the product crystallizes. The oil was decanted off and the solid was washed with hexanes and dried using a Büchner funnel to afford 4-bromo-N,N-diethyl-2-(2-oxopropyl)benzamide.

1. temperatureto slowly warm to room temperature
2. stirringThe reaction was stirred overnight
3. custompartitioned between 1 N 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. customcrystallizes
10. customThe oil was decanted off
11. washthe solid was washed with hexanes
12. customdried

ORD record

ord-4b877052ab2242b8844285712992402c

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139585B2