Ammonium Chloride → HCID 86693772, compound

HRID 245057Notes

Reaction equation

HRID 245057 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5]12[O:11][CH:10]1[CH2:9][O:8][CH2:7][CH2:6]2.[Cl-].[NH4+]>CO.O>[N:1]([C@@H:5]1[CH2:6][CH2:7][O:8][CH2:9][C@H:10]1[OH:11])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 120221313,7-Dioxabicyclo(4.1.0)heptane

Product 1

HCID 86693772HCID 86693772, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

Sodium azide (50.4 g, 775 mmol) is added to a stirring solution of 4,7-dioxabicyclo[4.1.0]heptane (9.7 g, 96.9 mmol) and ammonium chloride (23.0 g, 426 mmol) in methanol (484 mL) and water (97 mL), and heated to 65° C. under nitrogen for 18 h. The mixture is cooled to room temperature and water (200 mL) is added. The methanol is removed in vacuo and the remaining aqueous layer is extracted with EtOAc (3×). The organic portions are combined, dried over sodium sulfate, filtered, and concentrated in vacuo to yield the title compound as a tan oil (5.63 g, 41%). 1H NMR (400 MHz, DMSO-d6) δ 5.40-5.33 (m, 1H), 3.78-3.74 (m, 2H), 3.40-3.32 (m, 3H), 2.97-2.90 (m, 1H), 1.82-1.77 (m, 1H), 1.46-1.41 (m, 1H).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customThe methanol is removed in vacuo
  3. extractionthe remaining aqueous layer is extracted with EtOAc (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7374a4c7bb44a1c8776af300d8d4845
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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