Water → HCID 12046096, compound

HRID 2185004Notes

Reaction equation

HRID 2185004 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20].O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[S:9]([NH:23][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 120460952,6-dibroMobenzenesulfonyl chloride

Product 1

HCID 12046096HCID 12046096, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,6-dibromobenzenesulfonyl chloride (4.7 g, 14.0 mmol) in tetrahydrofuran (20 mL) was treated with potassium carbonate (5.8 g, 42 mmol) and t-butyl amine (1.2 g, 16.8 mmol). The resulting mixture was stirred at ambient temperature over 18 h then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 2,6-dibromo-N-(1,1-dimethylethyl)benzenesulfonamide (4.5 g, 87%) as the white solid, which was used without further purification. 1H NMR (CD3OD): δ1.22 (s, 9H), 7.22 (t, 1H), 7.85 (d, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-130841b9542e43e89989e2cfc377d50e
Source dataset
uspto-grants-2002_06
Patent number
US06399644B1

Reaction notes

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