Dimethylformamide → HCID 86607610, compound

Temperature

-78 °C

To a cooled solution of N,N-diisopropyl [4-(2-methylphenyl)benzamide (5.50 g, 19 mmol) in anhydrous THF (50 mL) at −70° C. was added dropwise a solution of tert-butyllithium, 1.7 M in pentane (13 mL, 22 mmol). The yellow mixture was stirred at −78° C. for 30 min, after which dimethylformamide (5.7 mL, 74 mmol) was added dropwise such that the internal temperature was maintained at −70° C. The resultant mixture was stirred at this temperature over 15 min and then was allowed to warm to RT and stood for 40 min. The brown solution was quenched by slow addition of saturated aqueous NH4Cl (100 mL), keeping the internal temperature below 0° C. The resulting mixture was diluted with diethyl ether (100 mL), and stirred at RT for 10 min. The organic phase was separated and aqueous phase was extracted with diethyl ether (3×60 mL). The combined organic phases were washed with brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure to give N,N-diisopropyl 2-formyl-4-(2-methylphenyl)benzamide as a yellow solid. MS (ESI, pos.ion) m/z: 324.2 (M+1)

1. temperaturewas maintained at −70° C
2. temperatureto warm to RT
3. waitstood for 40 min
4. customThe brown solution was quenched by slow addition of saturated aqueous NH4Cl (100 mL)
5. customthe internal temperature below 0° C
6. additionThe resulting mixture was diluted with diethyl ether (100 mL)
7. stirringstirred at RT for 10 min
8. customThe organic phase was separated
9. extractionaqueous phase was extracted with diethyl ether (3×60 mL)
10. washThe combined organic phases were washed with brine
11. dry with materialThe resulting organic solution was then dried over magnesium sulfate
12. concentrationconcentrated under reduced pressure

ORD record

ord-597fec1eee1f4430a192c446a2764642

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07759337B2