Water → 2-{[1-(Phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide

HRID 916629Notes

Reaction equation

HRID 916629 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C)C=O>[C:17]1([S:14]([N:9]2[C:10]3[C:6](=[C:5]([O:4][CH2:3][CH2:2][N:23]=[N+:24]=[N-:25])[CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 104047244-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-Indole

Product 1

HCID 120184382-{[1-(Phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

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 1 N 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.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed sequentially with 1 N HCl, H2O and saturated NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cae6e281e5b4b2fa02639a34589f702
Source dataset
uspto-grants-2007_09
Patent number
US07271180B2

Reaction notes

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