Benzenesulfonyl chloride → N-Benzo[b]thiophen-2-yl-benzenesulfonamide

HRID 57148Notes

Reaction equation

HRID 57148 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[S:12]1[C:16]([NH2:17])=[CH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]1=2>N1C=CC=CC=1>[S:12]1[C:16]([NH:17][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]1=2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 66906726Benzo[b]thiophen-2-amine hydrochloride

Product 1

HCID 57920397N-Benzo[b]thiophen-2-yl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (0.661 mL, 5.15 mmol) was added to a solution of compound 1-C (0.87 g, 4.69 mmol) in pyridine (10 mL) at 0° C. The ice bath was removed and the solution was stirred at ambient temperature for 2 h. The solvent was evaporated in vacuo, and the residue was partitioned between 2N HCl and dichloromethane. The organic layer was dried over magnesium sulfate and the solvent evaporated in vacuo. The residue was pre-absorbed on silica gel and purified by flash column chromatography, eluting with a gradient of ethyl acetate (10-50%) in heptane, to afford compound 1-D as a colorless solid (1.19 g, 88%). 1H-NMR (CDCl3): δ 6.96 (s, 1H), 7.25-7.34 (m, 2H), 7.44-7.49 (m, 2H), 7.55-7.66 (m, 3H), 7.84-7.88 (m, 2H); MS: m/z 290.1 (MH+).

Workup

  1. customThe ice bath was removed
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was partitioned between 2N HCl and dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe residue was pre-absorbed on silica gel
  7. custompurified by flash column chromatography
  8. washeluting with a gradient of ethyl acetate (10-50%) in heptane
  9. customto afford compound 1-D as a colorless solid (1.19 g, 88%)

Sources & evidence

ORD record
ord-aa53776ca5294cfd88ddad8027d33db4
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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