Trifluoromethanesulfonic anhydride → HCID 19029084, compound

HRID 2255921Notes

Reaction equation

HRID 2255921 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][N:17]1[C:22]([CH3:23])=[CH:21][C:20](O)=[CH:19][C:18]1=[O:25]>C(Cl)Cl>[CH3:16][N:17]1[C:22]([CH3:23])=[CH:21][C:20]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:19][C:18]1=[O:25]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 546761184-Hydroxy-1,6-dimethyl-1,2-dihydropyridin-2-one

Product 1

HCID 19029084HCID 19029084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulphonic anhydride (0.85 ml, 5 mM) was added dropwise to a stirred solution of 1,6-dimethyl-4-hydroxypyridin-2-one [0.7 g, 5 mM] (obtainable as described by Castillo et al., Bull. Soc. Chim. France, 1982, 257) in dry methylene chloride (15 ml). The resulting solution was kept at room temperature for 18 hours, washed with aqueous sodium carbonate solution, dried (MgSO4) and the solvent evaporated. The residual solid was purified by flash chromatography (Merck 9385) using ether as eluant to give 1,6-dimethyl-4-(trifluoromethanesulphonyloxy)-2-pyridone as a solid (0.67 g), m.p. 65°-67° C.; NMR: 2.41(3H,s, CH3) 3.53(3H,s, NCH3), 6.05(1H,s, CH), 6.38(1H,s, CH).

Workup

  1. washwashed with aqueous sodium carbonate solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent evaporated
  4. customThe residual solid was purified by flash chromatography (Merck 9385)

Sources & evidence

ORD record
ord-ab4671699b7740a89e9b41943bab2d9a
Source dataset
uspto-grants-1997_08
Patent number
US05654298

Reaction notes

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