HCID 22406979, compound → HCID 67771309, compound

HRID 440327Notes

Reaction equation

HRID 440327 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.OC([C:19]1[S:20][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:22][N:23]=1)C1CC1>CC(C)=O>[O:3]=[C:2]1[CH2:4][CH:1]1[C:19]1[S:20][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 22406979HCID 22406979, compoundHCID 131709961Jones' reagent

Product 1

HCID 67771309HCID 67771309, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (0.63 mL, 1.69 mmol, 2.67M) was added dropwise to a 0° C. solution of 2-(1-hydroxy-1-cyclopropylmethyl)-5-thiazole sulfonamide (0.33 g, 1.4 mmol) in acetone (5 mL). The ice bath was removed and the solution stirred for 30 min. The reaction was quenched with a few drops of isopropanol and the acetone removed in vacuo. The residue was taken up in water and extracted with EtOAc. The combined extracts were dried (MgSO4), concentrated and purified by flash chromatography using 30% EtOAc/hexane to give 0.23 g (72%) of 2-(1-ketocyclopropyl)-5-thiazole sulfonamide as a white solid.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched with a few drops of isopropanol
  3. customthe acetone removed in vacuo
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-f967181a3c074444904bb3d67db95c31
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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