Pyridine → 4,4,4-trifluoro-N-methoxy-N-methylbutanamide
Reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5](Cl)=[O:6].Cl.[CH3:11][O:12][NH:13][CH3:14].N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5]([N:13]([O:12][CH3:11])[CH3:14])=[O:6]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
4,4,4-Trifluorobutyric acid chloride (6.4 g from above) in CH2Cl2 (80 ml) was treated with O,N-dimethylhydroxylamine hydrochloride (60.0 mmol, 5.85 g). The mixture was cooled to 0° C., then treated with pyridine (160.0 mmol, 12.9 ml), then allowed to warm to room temperature overnight. The mixture was diluted with CH2Cl2 (200 ml), then washed with brine(2×50 ml). Solvent was removed from the volatile product by simple distillation at atmospheric pressure to provide 20 g of 4,4,4-trifluoro-N-methoxy-N-methyl butyramide, which may be used without further purification. 1H NMR (CDCl3) δ3.70 (3H, s), 3.19 (3H, s), 2.78-2.65 (2H, m), 2.57-2.40 (2H, m).
Workup
- temperatureto warm to room temperature overnight
- washwashed with brine(2×50 ml)
- customSolvent was removed from the volatile product by simple distillation at atmospheric pressure
Sources & evidence
- ORD record
- ord-2baf3009f6554835aa84d5e76a58cf86
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610730B2
Reaction notes
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