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Sodium Azide → 1,2-Di-O-(n-hexadecyl)-3-O-(3-azido-2-hydroxypropyl)-glycerol

HRID 2058394
Notes
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Reaction equation

HRID 2058394 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:21][CH2:22][CH:23]([CH2:41][O:42][CH2:43][CH:44]1[O:46][CH2:45]1)[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>O.O1CCOCC1>[CH2:5]([O:21][CH2:22][CH:23]([CH2:41][O:42][CH2:43][CH:44]([OH:46])[CH2:45][N:1]=[N+:2]=[N-:3])[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 33557Sodium Azide2×HCID 234661141,2-Di-O-(n-hexadecyl)-3-O-(2,3-epoxypropyl)-glycerol

Product 1

HCID 234660851,2-Di-O-(n-hexadecyl)-3-O-(3-azido-2-hydroxypropyl)-glycerolYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium azide (0.5 g., 7.7 mmoles) in water (5 ml.) was added to a refluxing solution of 1,2-di-O-(n-hexadecyl)-3-O-(2,3-epoxypropyl)-glycerol (3.3 g., 5.5 mmoles) in 1,4-dioxane (100 ml.), and the resulting solution stirred at reflux for 16 hours. Since the reaction was not yet complete, additional sodium azide (0.5 g., 7.7 mmoles) was added and the reaction stirred at reflux for another 16 hours. The reaction solution was then cooled, concentrated in vacuo, diluted with water (100 ml.) and extracted with ether (3×100 ml.). The combined ether extract was washed with water (100 ml.), dried (MgSO4), filtered and evaporated in vacuo to an oil which solidified on standing [2.2 g., 62% yield, ir (CHCl3) 2105 cm-1 ].

Workup

  1. temperatureat reflux for 16 hours
  2. stirringthe reaction stirred
  3. temperatureat reflux for another 16 hours
  4. temperatureThe reaction solution was then cooled
  5. concentrationconcentrated in vacuo
  6. additiondiluted with water (100 ml.)
  7. extractionextracted with ether (3×100 ml.)
  8. extractionThe combined ether extract
  9. washwas washed with water (100 ml.)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated in vacuo to an oil which

Sources & evidence

ORD record
ord-79713d5e080c47dba9f2784b9d949d1a
Source dataset
uspto-grants-1980_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04215146

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes