Ammonia → 4-Bromo-2-chlorobenzenesulfonamide

HRID 1098751Notes

Reaction equation

HRID 1098751 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1.[NH3:13].C(OCC)(=O)C.O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:13])(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 8857Ethyl AcetateHCID 27347664-Bromo-2-chlorobenzenesulfonyl chloride

Product 1

HCID 27347644-Bromo-2-chlorobenzenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-chlorobenzenesulfonyl chloride (2.50 g, 8.45 mmol) in THF (25 ml) was added a solution of ammonia (25%, 6.3 ml, 84.5 mmol). The reaction mixture was stirred for 4 h at RT. Ethyl acetate (70 ml) and water (50 mL) were added. The organic phase was separated and washed with hydrochloric acid (1 M, 50 ml) and brine (2×30 ml) and dried over sodium sulfate. After evaporation the product was obtained as a white solid (2.05 g, 90%) which was used in the next step without further purification.

Workup

  1. customThe organic phase was separated
  2. washwashed with hydrochloric acid (1 M, 50 ml) and brine (2×30 ml)
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation the product

Sources & evidence

ORD record
ord-f8ce2044d6b6470ba4d1e404f4dfdf2e
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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