Dimethylformamide → HCID 19764416, compound

HRID 1885466Notes

Reaction equation

HRID 1885466 reaction equation
[CH2:1]([O:17][CH2:18][C:19]1[C:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=C(C)C=C[C:20]=1S([O-])(=O)=O)[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][CH3:16].C(O)CC.[N-:42]=[N+:43]=[N-:44].[Na+].CN(C)C=O>O>[N:42]([CH2:20][CH:19]([CH2:18][O:17][CH2:1][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][CH3:16])[CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N+:43]=[N-:44]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86746122HCID 86746122, compound

Product 1

HCID 19764416HCID 19764416, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 16.3 g of 2-[(hexadecyloxy)methyl]-3-(phenylmethoxy)-4-methylbenzenesulfonate-1-propanol, 9.22 g of sodium azide and 130 ml of N,N-dimethylformamide is stirred at 80° C. for 3.5 hours and then at room temperature overnight. The mixture is poured into water and extracted with ether. The ether layer is dried and the solvent removed. The residue is purified by chromatography, to give 8.9 g of the desired compound as an oil.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionextracted with ether
  4. dry with materialThe ether layer is dried
  5. customthe solvent removed
  6. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-d1e29713a2714e06a996db9bdb355579
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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