Water → HCID 67345591, compound

HRID 1671606Notes

Reaction equation

HRID 1671606 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][C:8]1[C:9](=[O:14])[NH:10][CH:11]=[CH:12][CH:13]=1.ClC(Cl)(Cl)S(O[CH2:21][C:22]([F:25])([F:24])[F:23])(=O)=O.O>ClCCl>[CH3:7][C:8]1[C:9](=[O:14])[N:10]([CH2:21][C:22]([F:25])([F:24])[F:23])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 704812-Hydroxy-3-methylpyridineHCID 900272,2,2-Trifluoroethyl trichloromethanesulphonate

Product 1

HCID 67345591HCID 67345591, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cesium carbonate (11.4 g, 34.9 mmol) was added to a solution of 3-methylpyridin-2(1H)-one (3.81 g, 34.9 mmol) and 2,2,2-trifluoroethyl trichloromethanesulfonate (9.81 g, 34.9 mmol) in dichloromethane (80 mL). After 2 h, water was added. The mixture was extracted with ether (3×), and the combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane 25%→methanol/dichloromethane) gave the title compound (3.73 g). MS192.3 (M+1).

Workup

  1. extractionThe mixture was extracted with ether (3×)
  2. dry with materialthe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% dichloromethane 25%→methanol/dichloromethane)

Sources & evidence

ORD record
ord-3c6993b09bf7430d96205b6c20ca703a
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

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