Potassium Carbonate → HCID 63803879, compound

HRID 2054157Notes

Reaction equation

HRID 2054157 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([SH:9])=[N:7][CH:8]=1.F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([S:9][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 178506226HCID 178506226, compound

Product 1

HCID 63803879HCID 63803879, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-trifluoromethyl-pyridine-2-thiol (6.99 g, 39.0 mmol), 4-fluorobenzaldehyde (4.79 g, 38.6 mmol), anhydrous K2CO3 (8.16 g, 59.1 mmol) and DMF (70 mL) was heated at 110° C. for 18 h. The mixture was cooled to room temperature and partitioned between MTBE and water. The phases were separated. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to give a crude product which was purified by flash column chromatography (eluent: 5% MTBE in petroleum ether). Evaporation of the appropriate fractions gave the product (9.47 g, 87% yield). 1H NMR (CDCl3) δ 10.06 (s, 1H), 8.69-8.66 (m, 1H), 7.97-7.92 (m, 2H), 7.78-7.72 (m, 3H), 7.23-7.16 (m, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between MTBE and water
  3. customThe phases were separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude product which
  8. customwas purified by flash column chromatography (eluent: 5% MTBE in petroleum ether)
  9. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-aade7da85b054679afdbb4e4882f4c5f
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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