Sodium Azide → 3-Azidomethyl-3-methyloxetane

HRID 259851

Reaction equation

HRID 259851 reaction equation
Cl[CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1.[N-:8]=[N+:9]=[N-:10].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N:8]([CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1)=[N+:9]=[N-:10]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 791123-(Chloromethyl)-3-methyloxetane

Product 1

HCID 111477193-Azidomethyl-3-methyloxetaneYield 93%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-chloromethyl-3-methyloxetane (10.1 g, 83.5 mmol), tetra-n-butylammonium bromide (0.308 g, 0.96 mmol), sodium azide (6.5 g, 100 mmol) and water (27 mL) was heated at about 96° C. to about 103° C. for 4.5 h, after which time gas chromatographic analysis of the mixture indicated that the reaction had reached completion. The mixture was cooled to ambient temperature, and extracted with methylene chloride (25 mL). The organic extract was passed through a column containing aluminum oxide (10 g), and the column was rinsed with additional methylene chloride. The solvent was evaporated to give 9.84 g (93% yield) of 3-azidomethyl-3methyloxetane (>99.5% purity by glc and NMR analysis). NMR: 1H NMR: δ1.32 (s, 3H), 3.52 (s, 2H), 4.25 & 4.35 (AB, J=6.0 Hz, 4H); 13C NMR: δ21.44, 58.33, 40.03, 79.76; glc Rt= 3.19 min.

Workup

  1. temperaturewas heated at about 96° C. to about 103° C. for 4.5 h
  2. extractionextracted with methylene chloride (25 mL)
  3. extractionThe organic extract
  4. additioncontaining aluminum oxide (10 g)
  5. washthe column was rinsed with additional methylene chloride
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-49ae46dc72e84376a7d655772ddf8277
Source dataset
uspto-grants-1996_06
Patent number
US05523424

Linked notes

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