Sodium Azide → HCID 86674040, compound

HRID 573959Notes

Reaction equation

HRID 573959 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[C:27]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:23]Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N-:66]=[N+:67]=[N-:68].[Na+]>C(Cl)(Cl)Cl.CN(C)C=O>[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[C:27]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:23][N:66]=[N+:67]=[N-:68])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86654887HCID 86654887, compound

Product 1

HCID 86674040HCID 86674040, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3,4,5-Tris(octadecyloxy)benzyl chloride (4.02 g, 4.31 mmol) was dissolved in a mixed solvent of chloroform (40 mL) and N,N-dimethylformamide (120 mL), sodium azide (418 mg, 6.42 mmol) was added, and the mixture was stirred at 80° C. for 3 hr. After completion of the reaction, the reaction mixture was cooled to room temperature and washed with purified water (150 mL). The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, methanol was added thereto, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to give the title compound (3.92 g, 97.4%) as a white solid.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. washwashed with purified water (150 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure, methanol
  8. additionwas added
  9. filtrationthe precipitated solid was collected by filtration
  10. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-8c4539e8b463467493a34553810ec9c1
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

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