2,2,2-Trifluoro-N-(hydroxymethyl)acetamide → HCID 10422204, compound
Reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[CH:8][O:7][CH:6]=1)=[O:4].O[CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15]>S(=O)(=O)(O)O.C(OCC)(=O)C>[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[C:8]([CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[O:7][CH:6]=1)=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
To a suspension of N-methyl-3-furancaboxamide (0.404 g) (prepared as described in Synthetic Communications (1992), 22(16), 2381-92) in concentrated aqueous sulphuric acid (10 ml) at 0-5° C. was added N-(hydroxymethyl)-trifluoroacetamide (0.483 g). The suspension was allowed to warm to 20° C. and stirred for 1 h. The mixture was poured onto ice (100 g) and diluted with ethyl acetate (150 ml). The phases were separated and the organic phase washed with saturated sodium hydrogen carbonate (50 ml×2), brine (30 ml), dried (MgSO4) and filtered. The solvent was removed in vacuo to give a yellow solid. The residue was purified by silica SPE (10 g) eluting with 4:1 to 1:3 cyclohexane:ethyl acetate to give the title compound as a white solid (0.286 g).
Workup
- additionThe mixture was poured onto ice (100 g)
- customThe phases were separated
- washthe organic phase washed with saturated sodium hydrogen carbonate (50 ml×2), brine (30 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe solvent was removed in vacuo
- customto give a yellow solid
- customThe residue was purified by silica SPE (10 g)
- washeluting with 4:1 to 1:3 cyclohexane
Sources & evidence
- ORD record
- ord-c8c69cb74c7d4d80a9a72ada05e3c05d
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622464B2
Reaction notes
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