Dimethylformamide → N,N-Dimethyl 4-[4-(2,2,2-Trifluoroacetylamino)phenyl]butanamide
Reaction equation
S(Cl)(Cl)=O.[F:5][C:6]([F:23])([F:22])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])=[CH:12][CH:11]=1)=[O:8].[CH3:24][N:25](C=O)[CH3:26]>>[CH3:24][N:25]([CH3:26])[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]([F:23])([F:22])[F:5])=[CH:11][CH:12]=1Participants
Conditions
- Temperature
- -5 °C
Procedure
Thionyl chloride (71 mg, 0.60 mmol) was added slowly to a solution of 4-[4-(2,2,2-Trifluoroacetylamino)phenyl]butanoic acid (Formula 45) (0.15 g, 0.55 mmol) in DMF (5 mL) cooled at −5° C. The mixture was stirred for an additional 1 hour at −5° C. Excess dimethylamine (freshly distilled from its 40% aqueous solution) was added to the reaction medium. The second mixture was stirred for an additional 1 hour. Ethyl acetate (50 mL) was added to the mixture, which was washed with brine (2×50 ml). The organic layer was dried over MgSO4, and concentrated to yield N,N-Dimethyl 4-[4-(2,2,2-Trifluoroacetylamino)phenyl]butanamide (Formula 46) (0.17 g, quant.) as a yellowish solid. 1H NMR 9.70 (br s, 1H), 7.55 (d, 2H, J=8.6 Hz), 7.11 (d, 2H, J=8.6 Hz), 2.91 (s, 3H), 2.89 (s, 3H), 2.60 (t, 2H, J=7.7 Hz), 2.27 (t, 2H, J=7.7 Hz), 1.89 (p, 2H, J=7.7 Hz).
Workup
- distillationExcess dimethylamine (freshly distilled from its 40% aqueous solution)
- additionwas added to the reaction medium
- stirringThe second mixture was stirred for an additional 1 hour
- additionEthyl acetate (50 mL) was added to the mixture, which
- washwas washed with brine (2×50 ml)
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5275731f3ef0494cb3ee2d8d4ab7d4ca
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126941B2
Reaction notes
Loading…