4-Chlorobenzenesulfonyl chloride → HCID 12206222, compound

HRID 1929746Notes

Reaction equation

HRID 1929746 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:12]=[N+:13]=[N-:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 12206222HCID 12206222, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chlorobenzenesulfonyl chloride (5.28 g) in tetrahydrofuran (25 mL) was added a solution of sodium azide (1.79 g) in water (12.5 mL) and the mixture was stirred at room temperature overnight. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give 4-chlorobenzenesulfonyl azide (4.27 g, yield: 78%) as a colorless liquid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-eb661882f34b48b7b0234286a3d45d92
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

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