Water → HCID 86679334, compound

HRID 929268Notes

Reaction equation

HRID 929268 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[N+:12]=[N-:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18].O>CN(C=O)C>[CH2:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[N+:12]=[N-:13])(=[O:9])=[O:10])=[CH:4][CH:3]=1)[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 20397841HCID 20397841, compound

Product 1

HCID 86679334HCID 86679334, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-hydroxybenzenesulfonyl azide synthesized in Synthetic example 2 (1.72 g, 8.63 mmol, and 1.00 Eq) was dissolved in DMF (17 mL), and then sodium hydroxide (354 mg, 8.85 mmol, and 1.03 Eq) and allylbromide (14.0 g, 116 mmol, and 13.4 Eq) were added thereto. The solution was stirred at room temperature for 16 hours and water (50 mL) was added thereto, followed by extraction with diethylether (3×20 mL). The obtained organic layer was dried with sodium sulfate and the organic solvent was removed by the evaporator (30° C.). The product was purified by column chromatography (hexane/ethyl acetate 10:1) to obtain 4-allyloxybenzenesulphonyl azide as pale yellow oil (0.89 g, and 32%).

Workup

  1. extractionfollowed by extraction with diethylether (3×20 mL)
  2. dry with materialThe obtained organic layer was dried with sodium sulfate
  3. customthe organic solvent was removed by the evaporator (30° C.)
  4. customThe product was purified by column chromatography (hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-651536da65034f0dbb9ac3f442f155ab
Source dataset
uspto-grants-2016_03
Patent number
US09291908B2

Reaction notes

Loading…