Potassium Carbonate → HCID 53857759, compound

HRID 1977457Notes

Reaction equation

HRID 1977457 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11](O)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]1[O:22][C@@H:21]1[CH2:23]OS(C1C=C([N+]([O-])=O)C=CC=1)(=O)=O>>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:23][C@@H:21]2[O:22][CH2:20]2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 6422181-benzyl-1H-pyrazol-4-ol

Product 1

HCID 53857759HCID 53857759, compoundYield 73.1%

Procedure

1-Benzyl-4-hydroxypyrazole (2 g, 11.5 mmol), potassium carbonate(3.2 g, 23 mmol), and (2s)-glycidyl-3-nitrobenzenesulfonate (2.98 g, 11.5 mmol) were slurried in actone (300 ml) at reflux for 17 hours. The acetone was removed in vacuo, the residue extracted from brine with chloroform, and dried over sodium sulfate. The solvent was removed again and the residue purified by column chromatography (silica gel, chloroform→1% methanol/chloroform) to yield product (1.8 g, 68%). MS, NMR.

Workup

  1. temperatureat reflux for 17 hours
  2. customThe acetone was removed in vacuo
  3. extractionthe residue extracted from brine with chloroform
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed again
  6. customthe residue purified by column chromatography (silica gel, chloroform→1% methanol/chloroform)

Sources & evidence

ORD record
ord-56d2d6921b5a497f9497609e5dabc569
Source dataset
uspto-grants-2001_05
Patent number
US06232337B1

Reaction notes

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