Potassium Carbonate → HCID 59591433, compound

HRID 1963017Notes

Reaction equation

HRID 1963017 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH2:7]Br)[S:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[F:15][C:16]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21]([F:26])[C:17]=1[C:18]([NH2:20])=[O:19]>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH2:7][O:25][C:24]2[C:16]([F:15])=[C:17]([C:21]([F:26])=[CH:22][CH:23]=2)[C:18]([NH2:20])=[O:19])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 451201362,6-Difluoro-3-hydroxybenzamideHCID 59591444HCID 59591444, compound

Product 1

HCID 59591433HCID 59591433, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-(bromomethyl)thiazole (1.57 g, 6.10 mmol) in DMF (15 ml) was added dried K2CO3 (2.95 g, 21.38 mmol) followed by addition of 2,6-difluoro-3-hydroxybenzamide (1.05 g, 6.10 mmol). The resulting reaction mass was stirred at room temperature for 2 h. After the completion of the reaction (TLC monitoring), ice-cold water was added (50 ml) followed by extraction with EtOAc (3×100 ml). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was washed with ether and the solid thus obtained was filtered to get the desired product (1.56 g, 74%).

Workup

  1. customThe resulting reaction mass
  2. customAfter the completion of the reaction (TLC monitoring), ice-cold water
  3. additionwas added (50 ml)
  4. extractionfollowed by extraction with EtOAc (3×100 ml)
  5. washThe combined organics was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washThe residue was washed with ether
  10. customthe solid thus obtained
  11. filtrationwas filtered

Sources & evidence

ORD record
ord-8daae53b055841e1bff95d61814d1f65
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

Loading…