Sodium Iodide → HCID 86632158, compound

HRID 242728Notes

Reaction equation

HRID 242728 reaction equation
Cl[CH2:2][C@H:3]([OH:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](/[CH:11]=[CH:12]/[C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[CH:6]=1.[Na+].[I-].[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C>[N:24]([CH2:2][C@H:3]([OH:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](/[CH:11]=[CH:12]/[C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[CH:6]=1)=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 68947443HCID 68947443, compound

Product 1

HCID 86632158HCID 86632158, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (R,E)-1-chloro-3-(3-(2,6-dichlorostyryl)phenyl)propan-2-ol (0.67 g, 1.96 mmol) in DMF (20 mL) was added NaI (˜25 mg, 0.16 mmol) and NaN3 (0.64 g, 9.8 mmol) and the reaction mixture was heated at 75° C. overnight. After cooling to room temperature, the mixture was partitioned between EtOAc and water. The combined organics were washed with water, 5% aqueous LiCl and brine, filtered through Na2SO4 and concentrated under reduced pressure to give (R,E)-1-azido-3-(3-(2,6-dichlorostyryl)phenyl)propan-2-ol. This material was used in the next synthetic step without purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe combined organics were washed with water, 5% aqueous LiCl and brine
  4. filtrationfiltered through Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13a651904d5344b39bf30be299788d62
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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