Ammonium Chloride → HCID 72410014, compound

HRID 723465Notes

Reaction equation

HRID 723465 reaction equation
[OH:1][CH:2]1[CH:8]2[CH:6]([O:7]2)[CH2:5][N:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1.[N-:14]=[N+:15]=[N-:16].[Na+].[NH4+].[Cl-]>COCCO>[N:14]([CH:8]1[CH:2]([OH:1])[CH2:3][N:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH:6]1[OH:7])=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 72410012HCID 72410012, compound

Product 1

HCID 72410014HCID 72410014, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of Compound 239G (2.0 g, 10.7 mmol) in 2-methoxyethanol (40 mL) was added NaN3 (3.5 g, 53.4 mmol) and NH4Cl (2.3 g, 42.72 mmol). The reaction mixture was heated at 125° C. overnight. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was taken into EtOAc (50 mL), washed with water (10 mL×2) and dried over anhydrous Na2SO4. Concentration in vacuo followed by flash chromatography (hexane-EtOAc: 1:1 to 1:2) on silica gel afforded 0.64 g of 239I (higher Rf) as a crystalline material. The stereochemistry was confirmed by a single x-ray crystallographic determination.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure
  3. washwashed with water (10 mL×2)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-0a821bc6e6cc40f5951386f3cda30fec
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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