Dimethylformamide → HCID 15253644, compound

HRID 1908241Notes

Reaction equation

HRID 1908241 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C@@H:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[OH:8].CN(C=O)C>O>[N:1]([CH2:6][C@@H:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[OH:8])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 12300420(R)-2-Chloro-1-(4-fluorophenyl)ethanol

Product 1

HCID 15253644HCID 15253644, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (41.8 g, 642 mmol) was added to a solution consisting of (1R)-2-chloro-1-(4-fluoro-phenyl)-ethanol (37.4 g, 214 mmol) and DMF (214 mL) at rt. The reaction mixture was heated to 100° C. for 3 h, diluted with water (500 mL), and extracted with EtOAc (700 mL). The organic layer was washed with brine (500 mL), and the organic layer dried (MgSO4), filtered, and concentrated, giving the title compound as a yellow liquid, which was used without further purification (39 g, 100%).

Workup

  1. extractionextracted with EtOAc (700 mL)
  2. washThe organic layer was washed with brine (500 mL)
  3. dry with materialthe organic layer dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3fc52f674cb0477b8c214a760d0e7e79
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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