Lithium azide → 1,3-Dioleyloxy-2-propyl azide

HRID 724764Notes

Reaction equation

HRID 724764 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([CH2:33][O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]/[CH:43]=[CH:44]\[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N-:53]=[N+:54]=[N-:55].[Li+]>CN(C)C=O>[CH2:1]([O:19][CH2:20][CH:21]([N:53]=[N+:54]=[N-:55])[CH2:33][O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]/[CH:43]=[CH:44]\[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 867518541,3-O-dioleyl-2-O-(p-toluenesulfonyl)glycerol

Product 1

HCID 867518551,3-Dioleyloxy-2-propyl azideYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 150 mg (80%) of the above 1,3-O-dioleyl-2-O-(p-toluenesulfonyl)glycerol, 30 mg (0.6 mmol) of lithium azide, and 5 ml of N,N-dimethylformamide was stirred at 100° C. for 2 hours. After cooling, the solvent was distilled off and the residue was diluted with water and extracted with ether. The extract was washed with water, dried, and concentrated to provide 125 mg (99%) of 1,3-dioleyloxy-2-propyl azide as light-brown oil.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off
  3. additionthe residue was diluted with water
  4. extractionextracted with ether
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3ea7d9c7611d418ab5920e33a6c4f8bd
Source dataset
uspto-grants-1998_01
Patent number
US05705188

Reaction notes

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