Acetonitrile → HCID 61373088, compound

HRID 1159189Notes

Reaction equation

HRID 1159189 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH:11]2[CH2:13]O2)=[CH:8][CH:7]=1.[Cl-].[NH4+].[C:18](#N)C>O>[N:1]([CH2:18][CH2:13][CH2:11][O:10][C:9]1[CH:14]=[CH:15][C:6]([Cl:5])=[CH:7][CH:8]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14448268HCID 14448268, compound

Product 1

HCID 61373088HCID 61373088, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium azide (0.977 g, 15 mmol) in water (1 ml) was added to a solution of rac-(4-chlorophenoxy)oxirane (1.85 g, 10 mmol) in acetonitrile (11 ml). The mixture was heated to reflux for overnight. Saturated ammonium chloride solution (20 ml) was added and the mixture was extracted with ethyl acetate (3 times 25 ml). The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by chromatography (SiO2, ethyl acetate/heptane=1:1) to yield a colorless liquid (1.73 g, 76%); MS (EI): 227.1 ((M+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for overnight
  3. extractionthe mixture was extracted with ethyl acetate (3 times 25 ml)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, ethyl acetate/heptane=1:1)

Sources & evidence

ORD record
ord-58d3f68fe7bb449b816e2e482bd6935b
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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