Dimethylformamide → 3,3,3-Trifluoro-2,2-dimethyl-propionamide

Oxalyl chloride (140.8 mmol) was added dropwise to a solution of 3,3,3-trifluoro-2,2-dimethyl-propionic acid [889940-13-0] (128 mmol) in CH2Cl2 (128 mL) at 0° C. Added a few dr DMF until gas evolution was observed and then continued stirring for 30 min. After warming to rt and stirring overnight, the reaction mixture was concentrated (40° C., 00 mbar). The residue was dissolved in THF (128 mL), cooled to 0° C. and then slowly treated with a solution of concentrated aqueous ammonia (64 mL). After stirring at 0° C. for 30 min and then at rt for 4 h, the reaction mixture was concentrated to half its volume to give a thick white suspension. After filtering and drying, the title compound was obtained as a white solid. ESI-MS: [M+H]+ 156.

1. stirringstirring overnight
2. concentrationthe reaction mixture was concentrated (40° C., 00 mbar)
3. dissolutionThe residue was dissolved in THF (128 mL)
4. temperaturecooled to 0° C.
5. additionslowly treated with a solution of concentrated aqueous ammonia (64 mL)
6. stirringAfter stirring at 0° C. for 30 min
7. waitat rt for 4 h
8. concentrationthe reaction mixture was concentrated to half its volume
9. customto give a thick white suspension
10. filtrationAfter filtering
11. customdrying

ORD record

ord-b778f621d1474fa3ba94af52bb696b47

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357707B2