Reaction #2069971

ord-7ea0f066c6c249dfaf0dfbd177a60da6

Reaction equation

O=S(=O)(c1ccccc1)n1ccc2c(OCCCl)cccc21
4-(2-chloroethoxy)-1-(phenylsulfonyl)-1H-indole
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water
→
[N-]=[N+]=NCCOc1cccc2c1ccn2S(=O)(=O)c1ccccc1
title product
[N-]=[N+]=NCCOc1cccc2c1ccn2S(=O)(=O)c1ccccc1
2-{[1-(Phenylsulfonyl)-1H-Indole-4-yl]oxy}ethylazide

Reactants

O=S(=O)(c1ccccc1)n1ccc2c(OCCCl)cccc21
4-(2-chloroethoxy)-1-(phenylsulfonyl)-1H-indole
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionextracted with diethyl ether
  2. 2
    Washwashed sequentially with 1N HCl, H2O and saturated NaCl
  3. 3
    Dryingdried over MgSO4
  4. 4
    Concentrationconcentrated in vacuo

Procedure

A suspension of 4-(2-chloroethoxy)-1-(phenylsulfonyl)-1H-indole (3.35 g, 10 mmol) and sodium azide (1.95 g, 30 mmol) in anhydrous dimethylformamide is stirred under nitrogen for 20 hr at 60° C., poured into water and extracted with diethyl ether. The extracts are combined, washed sequentially with 1N HCl, H2O and saturated NaCl, dried over MgSO4 and concentrated in vacuo to afford the title product as an off-white solid, 3.3 g (96%), identified by NMR and mass spectral analyses.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07541358B2uspto-grants-2009_06