Sodium Azide → Benzenesulfonamide

HRID 1063944Notes

Reaction equation

HRID 1063944 reaction equation
C[C@@:2]1([S:12]([NH2:15])(=[O:14])=[O:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]1CCCBr.[N-]=[N+]=[N-].[Na+]>C1COCC1.O>[C:2]1([S:12]([NH2:15])(=[O:14])=[O:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 131725216HCID 131725216, compound

Product 1

HCID 7370BenzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
22 °C

Procedure

To a solution of 4-chloro-N-(2,5-dichlorophenyl)-N-[(R)-1-methyl-3-bromopropylbenzene-sulfonamide (1.188 g, 2.295 mmol) in THF/H2O (20/4, 24 mL) was added sodium azide (1.49 g, 22.9 mmol) at 22° C. The resulting mixture was allowed to stir at 22° C. for 4 days. The mixture was extracted with ether (3×60 mL). The combined organic extracts were washed with sat. NaHCO3, dried over MgSO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (1:9 ethyl acetate:hexanes) of the concentrate afforded 0.941 g of 4-chloro-N-(2,5-dichlorophenyl)-N-[(R)-1-methyl-3-azidopropyl]]benzenesulfonamide as a colorless oil in 94% yield.

Workup

  1. extractionThe mixture was extracted with ether (3×60 mL)
  2. washThe combined organic extracts were washed with sat. NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-726d481f325e4870b6c6a027d809b88a
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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