m-Bromobenzenesulphonyl chloride → HCID 57750916, compound

HRID 2283368Notes

Reaction equation

HRID 2283368 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[S:7]([NH2:10])(=[O:9])=[O:8].[Br:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1>N1C=CC=CC=1>[Br:11][C:12]1[CH:13]=[C:14]([S:18]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[S:7]([NH2:10])(=[O:9])=[O:8])(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 17943m-Bromobenzenesulphonyl chlorideHCID 20152693HCID 20152693, compound

Product 1

HCID 57750916HCID 57750916, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-amino-thiophene-2-sulfonic acid amide (100 mg, 0.56 mmol) and 3-bromo-benzenesulfonyl chloride (97 μL, 0.67 mmol) in anhydrous pyridine (3 mL) was stirred at room temperature for 17 hours. The solvent was removed in vacuo and the residue was taken up in dichloromethane (25 mL). The organic phase was washed with 1 M hydrochloric acid, saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography, using 4-6% methanol in dichloromethane as the eluent, gave 147.6 mg (66% yield) of the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. washThe organic phase was washed with 1 M hydrochloric acid, saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-967d71b8d8ce488b81e36eff54b42605
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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