Sodium Iodide → HCID 86719462, compound

HRID 1506826Notes

Reaction equation

HRID 1506826 reaction equation
Cl[CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C:16]3=[O:21])=[CH:11][CH:10]=2)[CH2:4]1.[I-:22].[Na+]>S1(CCCC1)(=O)=O.O>[I:22][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C:16]3=[O:21])=[CH:11][CH:10]=2)[CH2:4]1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 54762708HCID 54762708, compound

Product 1

HCID 86719462HCID 86719462, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
110 °C

Procedure

Under an atmosphere of nitrogen to a solution of 1.00 g of 4-[4-[(5R)-5-(chloromethyl)-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone (MW=310.74; 1 eq.) in 5.3 mL sulfolane were added 0.97 g of sodium iodide (MW=149.89; 2 eq.). The resulting reaction mixture was stirred for 20 h at 110° C. Then the resulting slurry was cooled to room temperature and diluted with 30 mL of water. After stirring for 1 h at ambient temperature, the crystal suspension was isolated by filtration and the filter cake was washed with 20 mL of water. After drying in vacuo at 30° C., 1.05 g of the crystalline title compound (MW=402.19) were isolated. Yield=81.4%.

Workup

  1. customThe resulting reaction mixture
  2. temperatureThen the resulting slurry was cooled to room temperature
  3. stirringAfter stirring for 1 h at ambient temperature
  4. customthe crystal suspension was isolated by filtration
  5. washthe filter cake was washed with 20 mL of water
  6. customAfter drying in vacuo at 30° C.

Sources & evidence

ORD record
ord-81bb467c54e84cfba18a2de6f15128a0
Source dataset
uspto-grants-2015_12
Patent number
US09221771B2

Reaction notes

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