Ammonium Chloride → HCID 80503395, compound

HRID 1927677Notes

Reaction equation

HRID 1927677 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[F:7][C:8]1[CH:9]=[C:10]([CH:15]2[CH2:17][O:16]2)[CH:11]=[CH:12][C:13]=1[F:14].C(OCC)(=O)C.CCCCCC>CO.O>[N:1]([CH2:17][CH:15]([C:10]1[CH:11]=[CH:12][C:13]([F:14])=[C:8]([F:7])[CH:9]=1)[OH:16])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 143729232-(3,4-Difluorophenyl)oxiraneHCID 21226206Ethyl acetate hexane

Product 1

HCID 80503395HCID 80503395, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium azide (625 mg, 9.6 mmol) followed by ammonium chloride (514 mg, 9.6 mmol) were added to a solution of 2-(3,4-difluorophenyl)oxirane (1 g, 6.4 mmol) in methanol (10 mL) and water (2.5 mL). After stirring at 80° C. overnight, the reaction mixture was concentrated to give a residue. The residue was partitioned between water and ethyl acetate. The organic phase was washed with brine, dried (sodium sulfate) and concentrated to give a residue. Chromatography of the residue over silica gel eluting with 10-50% ethyl acetate/hexane afforded 2-azido-1-(3,4-difluorophenyl)ethanol.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto give a residue
  3. customThe residue was partitioned between water and ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customto give a residue

Sources & evidence

ORD record
ord-eef8816634944769a906e9033a737dec
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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