Dimethyl Sulfoxide → HCID 59762233, compound

HRID 561903Notes

Reaction equation

HRID 561903 reaction equation
Cl[CH2:2][C@@H:3]([OH:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[N-:14]=[N+:15]=[N-:16].[Na+].CS(C)=O>O>[N:14]([CH2:2][C@@H:3]([OH:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 16216998(2S)-1-Chloro-3-(4-fluorophenoxy)propan-2-ol

Product 1

HCID 59762233HCID 59762233, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-1-Chloro-3-(4-fluoro-phenoxy)-propan-2-ol (5.0 g, 24.5 mmol), sodium azide (3.19 g, 49.0 mmol) and DMSO (25 mL) was stirred at 80° C. for 6 h. Then the reaction mixture was poured into water (100 mL), extracted with hexane-Et2O (1:1) mixture (2×100 mL). Extracts were washed with brine (100 mL), dried over Na2SO4 and evaporated. The residue was dried under vacuum at RT. Colorless oil, 4.83 g (22.9 mmol, 93%).

Workup

  1. extractionextracted with hexane-Et2O (1:1) mixture (2×100 mL)
  2. washExtracts were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was dried under vacuum at RT

Sources & evidence

ORD record
ord-01e58f36933e4bcaa2d8db7a9c81fa36
Source dataset
uspto-grants-2011_11
Patent number
US08063225B2

Reaction notes

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