Sodium Azide → 3-Azidomethyl-3-methyloxetane

HRID 890576Notes

Reaction equation

HRID 890576 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1([CH3:11])[CH2:10][O:9][CH2:8]1>O>[N:1]([CH2:6][C:7]1([CH3:11])[CH2:10][O:9][CH2:8]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 144860Oxetane, 3-(bromomethyl)-3-methyl-

Product 1

HCID 111477193-Azidomethyl-3-methyloxetaneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 5 liter jacketed flask equipped with a mechanical stirrer was charged with 1062 grams of sodium azide, 1972 ml of water, and 2450 grams of 3-bromomethyl-3-methyloxetane (supplied by AmeriBrom, Inc. of New York). This mixture was brought to reflux with vigorous mixing. After 48 hours the mixture was cooled to room temperature. The organic layer was separated off and washed three times with 1000 ml of water before being dried over molecular sieves to yield pure 3-azidomethyl-3-methyloxetane at 85% yield.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureto reflux with vigorous mixing
  3. customThe organic layer was separated off
  4. washwashed three times with 1000 ml of water
  5. custombefore being dried over molecular sieves

Sources & evidence

ORD record
ord-6836d8b4fdeb45fe84ff697f6bb6d70c
Source dataset
uspto-grants-2006_02
Patent number
US06997997B1

Reaction notes

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