Sodium Azide → HCID 16107468, compound

HRID 556214Notes

Reaction equation

HRID 556214 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]([F:42])([F:41])[C:7]([C:37]([F:40])([F:39])[F:38])([C:33]([F:36])([F:35])[F:34])[O:8][CH2:9][C:10]1([CH2:18][O:19][C:20]([C:29]([F:32])([F:31])[F:30])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])[CH2:15]OS(=O)(=O)[O:12][CH2:11]1>CC(C)=O>[N:1]([CH2:15][C:10]([CH2:9][O:8][C:7]([C:6]([F:5])([F:41])[F:42])([C:37]([F:38])([F:39])[F:40])[C:33]([F:34])([F:35])[F:36])([CH2:18][O:19][C:20]([C:21]([F:22])([F:24])[F:23])([C:25]([F:28])([F:27])[F:26])[C:29]([F:32])([F:31])[F:30])[CH2:11][OH:12])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 16107460HCID 16107460, compound

Product 1

HCID 16107468HCID 16107468, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (4.4 g, 66.9 mmol) was added to a stirred solution of compound 10 (21.2 g, 33.4 mmol) in dimethylformaldehyde (120 mL). The reaction mixture was stirred at 60° C. for 4 hours. The solvent was removed under vacuo and the residue was dissolved in tetrahydrofuran (120 mL). Sulfuric acid (0.87 mL) and water (0.32 mL) were added to the stirred tetrahydrofuran solution and the resulting mixture was stirred at room temperature for an additional hour. After removal the solvent, the residue was redissolved in dichloromethane (200 mL) and extracted with perfluorohexane (100 mL 4 times). The combined extraction was washed with dichloromethane (10 mL) and concentrated under vacuo to give the pure azide 11 as a clear oil (19.3 g, 97%). 1H NMR (400 MHz, CDCl3) δ 3.47 (s, 2H), 3.63 (s, 2H), 4.02 (s, 4H); 19F NMR (376 MHz, CDCl3) δ −73.21 (s); 13C NMR (100.7 MHz, CDCl3) δ 45.8, 49.8, 60.2, 66.8, 79.6 (m), 120.2 (q, J=293.3 Hz); MS (CI) m/z 598 (M++1, 72), 570 (100); HRMS (CI) Calcd for C13H10F18N3O3: 598.0435, Found: 598.0418.

Workup

  1. customThe solvent was removed under vacuo
  2. dissolutionthe residue was dissolved in tetrahydrofuran (120 mL)
  3. additionSulfuric acid (0.87 mL) and water (0.32 mL) were added to the stirred tetrahydrofuran solution
  4. stirringthe resulting mixture was stirred at room temperature for an additional hour
  5. customAfter removal the solvent
  6. dissolutionthe residue was redissolved in dichloromethane (200 mL)
  7. extractionextracted with perfluorohexane (100 mL 4 times)
  8. extractionThe combined extraction
  9. washwas washed with dichloromethane (10 mL)
  10. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-930765b770344c979e424d4d7bf1e6b2
Source dataset
uspto-grants-2011_11
Patent number
US08052961B2

Reaction notes

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