Sodium Iodide → HCID 21341522, compound

HRID 2185504Notes

Reaction equation

HRID 2185504 reaction equation
S([O:5][CH2:6][C@@H:7]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=O)(=O)C.[N-:24]=[N+:25]=[N-:26].[Na+].[I-].[Na+]>CN(C=O)C>[C:12]([O:11][C:9]([NH:8][C@@H:7]([C:6]([N:24]=[N+:25]=[N-:26])=[O:5])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 131723255HCID 131723255, compound

Product 1

HCID 21341522HCID 21341522, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The product from (B) (12.6 mmol) was dissolved in DMF (25 mL) and sodium azide (NaN3) (50 mmol) and sodium iodide (NaI) (50 mmol) were added. This solution was warmed at 50° C. for 24 hr then cooled to room temperature, washed with H2O (3×50 mL), extracted with EtOAc (2×50 mL) and washed with brine (1×25 mL). The organic layer was dried over Na2SO4, filtered dried to give the title compound (2.8 g, 77%) as an oil.

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with H2O (3×50 mL)
  3. extractionextracted with EtOAc (2×50 mL)
  4. washwashed with brine (1×25 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-3e092dff101541a797756f09557949dd
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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