Ammonium Hydroxide → 3,3,3-Trifluoro-2,2-dimethyl-propionamide

A solution of 3,3,3-trifluoro-2,2-dimethylpropionic acid (0.5 g, 3.20 mmol) in DCM (5 mL) was treated with oxalyl chloride (0.350 mL, 4.00 mmol) and 1 drop of DMF, stirred at RT for 1 h, added drop-wise to a solution of NH4OH (˜15M, 5 mL, ˜75 mmol) in THF (5 mL) and stirred at RT overnight. Solids were removed via filtration through diatomaceous earth, rinsed well with 4:1 DCM/THF, the filtrate saturated with solid NaCl, extracted with 4:1 DCM/THF (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 3,3,3-trifluoro-2,2-dimethylpropanamide (370 mg, 74%). 1H NMR (400 MHz, DMSO-d6): δ 7.42 (s, 1H), 7.35 (s, 1H), 1.29 (s, 6H).

1. stirringstirred at RT overnight
2. customSolids were removed via filtration through diatomaceous earth
3. washrinsed well with 4:1 DCM/THF
4. extractionthe filtrate saturated with solid NaCl, extracted with 4:1 DCM/THF (3×)
5. dry with materialthe combined organics were dried over Na2SO4
6. concentrationconcentrated to dryness

ORD record

ord-08afd0753be84632831fa4db7b803dcb

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382228B2