Dimethylformamide → HCID 19764416, compound

HRID 248156Notes

Reaction equation

HRID 248156 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-a9d2dbce3800437eb540b3fbe8bc6056
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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