Potassium Carbonate → HCID 2359066, compound

HRID 1255157Notes

Reaction equation

HRID 1255157 reaction equation
Cl[CH:2]([C:6](=[O:8])[CH3:7])[C:3](=O)[CH3:4].[C:9]([NH:12][C:13](=[O:22])[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[F:21])(=[S:11])[NH2:10].C([O-])([O-])=O.[K+].[K+]>CO>[C:6]([C:2]1[S:11][C:9]([NH:12][C:13](=[O:22])[C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:10][C:3]=1[CH3:4])(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 743283-Chloro-2,4-pentanedioneHCID 57243198HCID 57243198, compound

Product 1

HCID 2359066HCID 2359066, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 3-chloro-2,4-pentanedione (670 mg, 4.88 mmol), N-carbamothioyl-2,6-difluorobenzamide (1.08 g, 5.0 mmol) and K2CO3 (0.8 g) in 20 mL of MeOH was stirred at reflux for 5 hours. The reaction was cooled to room temperature, and concentrated under reduced pressure. The residue was taken up with EtOAc. The solution was washed with water, dried (Na2SO4), filtered and concentrated. Purification on silica gel gave N-(5-Acetyl-4-methylthiazol-2-yl)-2,6-difluorobenzamide (1.0 g, 71%) as a white solid.

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationconcentrated under reduced pressure
  3. washThe solution was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on silica gel

Sources & evidence

ORD record
ord-b07d0797362e4784baf8e4cfaeeb70c1
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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