Sodium Sulfate → HCID 14424362, compound

HRID 414227Notes

Reaction equation

HRID 414227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13]3[S:14][C:15](SC)=[CH:16][CH:17]=3)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.Cl[C:21]1C=CC=C(C(OO)=O)C=1.[S:31]([O-:35])([O-])(=O)=[O:32].[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:13]3[S:14][C:15]([S:31]([CH3:21])(=[O:35])=[O:32])=[CH:16][CH:17]=3)=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acidHCID 14424318HCID 14424318, compound

Product 1

HCID 14424362HCID 14424362, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-(4-fluorophenyl)-5-(5-methylthiothien-2-yl)thiazole (1.07 g, 0.0035 mole) in methylene chloride (50 mL) was added dropwise a solution of m-chloroperbenzoic acid (1.7 g, 0.0084 mole) in methylene chloride (25 mL). After complete addition the mixture was stirred at room temperature for approximately 18 hours. Approximately 100 mL of an aqueous 10% sodium sulfate solution was added, and the mixture was stirred for about 15 minutes. The mixture was washed in succession with an aqueous, saturated, sodium bicarbonate solution, water, and an aqueous, saturated, sodium chloride solution. A thin layer chromatograph of the organic phase indicated that starting material remained. Thus the washed organic phase was diluted with methylene chloride, and an additional 1.7 grams of m-chloroperoxybenzoic acid was added. This mixture was stirred and heated at reflux until only one spot was seen by thin layer chromatography. Approximately 100 mL of an aqueous 10% sodium sulfate solution was added, and the mixture was stirred for about 15 minutes. This mixture was washed in succession with an aqueous, saturated sodium bicarbonate solution, water, and an aqueous, saturated, sodium chloride solution. The washed organic phase was evaporated under reduced pressure, leaving a solid residue. This residue was purified by column chromatography on silica gel, elution with methylene chloride:ethyl acetate (19:1), to yield 0.59 g of 2-(4-fluorophenyl)-5(5-methylsulfonylthien-2-yl)thiazole as a solid, mp 183°-184° C.

Workup

  1. additionAfter complete addition the mixture
  2. stirringthe mixture was stirred for about 15 minutes
  3. washThe mixture was washed in succession with an aqueous, saturated, sodium bicarbonate solution, water
  4. additionThus the washed organic phase was diluted with methylene chloride
  5. additionan additional 1.7 grams of m-chloroperoxybenzoic acid was added
  6. stirringThis mixture was stirred
  7. temperatureheated
  8. temperatureat reflux until only one spot
  9. additionApproximately 100 mL of an aqueous 10% sodium sulfate solution was added
  10. stirringthe mixture was stirred for about 15 minutes
  11. washThis mixture was washed in succession with an aqueous, saturated sodium bicarbonate solution, water
  12. customThe washed organic phase was evaporated under reduced pressure
  13. customleaving a solid residue
  14. customThis residue was purified by column chromatography on silica gel, elution with methylene chloride:ethyl acetate (19:1)

Sources & evidence

ORD record
ord-a118a2dcbba342dd9a505dda9109475d
Source dataset
uspto-grants-1988_12
Patent number
US04791124

Reaction notes

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