Sodium hydride → HCID 118208536, compound

HRID 595227Notes

Reaction equation

HRID 595227 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[H-].[Na+].[OH:15][CH:16]([CH2:20][N:21]1[CH:25]=[C:24]([I:26])[CH:23]=[N:22]1)[C:17]([NH2:19])=[O:18]>C(=O)(OCC)OCC.[Cl-].[NH4+]>[I:26][C:24]1[CH:23]=[N:22][N:21]([CH2:20][CH:16]2[O:15][C:1](=[O:2])[NH:19][C:17]2=[O:18])[CH:25]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 118209008HCID 118209008, compound

Product 1

HCID 118208536HCID 118208536, compound

Reagents, catalysts & solvents 2

HCID 7766Diethyl CarbonateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
50 °C

Procedure

1,1′-Carbonyldiimidazole (3.5 g, 21 mmol) and sodium hydride (0.85 g, 21 mmol, 60 wt %) were added to a mixture of 2-hydroxy-3-(4-iodo-1H-pyrazol-1-yl)propanamide (2 g, 7 mmol) in diethyl carbonate (50 mL). The mixture was stirred at 50° C. for 5 hours. After cooling to room temperature, the mixture was diluted with aqueous ammonium chloride solution and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc) to afford 5-((4-iodo-1H-pyrazol-1-yl)methyl)oxazolidine-2,4-dione. MS ESI calc'd. for C7H7IN3O3 [M+H]+ 308. found 308. 1H NMR (400 MHz, CDCl3) δ 7.55 (s, 1H), 7.50 (s, 1H), 5.16 (s, 1H), 4.68 (d, J=4 Hz, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-34df5594c4ef4ad1915fa860e705297a
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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