Sodium Azide → HCID 18625812, compound

HRID 1859953Notes

Reaction equation

HRID 1859953 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][CH:14]=1)(=O)=O>CN(C)C=O>[N:1]([CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH:20]([CH2:26][CH2:27][O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:18]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 18625877HCID 18625877, compound

Product 1

HCID 18625812HCID 18625812, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium azide (0.29 g) was added to a solution of ethyl 3-[4-(2-methanesulfonyloxyethoxy)phenyl]-2-(2-phenoxyethyl)propionate, which is the product of Reference example 3(g), in dimethylformamide (8 ml). The mixture was stirred at 70° C. for 2 hours. At the end of this time the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and then concentrated to afford the desired compound (546 mg) as a syrup.

Workup

  1. customAt the end of this time the reaction mixture was partitioned between ethyl acetate and water
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cec46388a8d34584819bf32840d79ef5
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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