p-Bromobenzenesulfonyl chloride → N-(Benzo[b]thiophen-2-yl)-4-bromobenzenesulfonamide

HRID 57172Notes

Reaction equation

HRID 57172 reaction equation
Cl.[S:2]1[C:6]([NH2:7])=[CH:5][C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]1=2.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1.C(Cl)Cl>[S:2]1[C:6]([NH:7][S:19]([C:16]2[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][CH:15]=2)(=[O:21])=[O:20])=[CH:5][C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]1=2

Participants

5

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 66906726Benzo[b]thiophen-2-amine hydrochloride

Product 1

HCID 57920502N-(Benzo[b]thiophen-2-yl)-4-bromobenzenesulfonamideYield 73.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 1-C (9.28 g, 49.9 mmol) in pyridine (100 mL) and methylene chloride (50 mL), cooled on an ice bath, was added 4-bromobenzene-1-sulfonyl chloride (12.8 g, 49.9 mmol), portion-wise over a period of 4 minutes. The reaction mixture was allowed to warm to ambient temperature and stirred for 18 h. The reaction mixture was concentrated under reduced pressure, the crude residue partitioned between EtOAc (500 mL) and 1N HCl (250 mL), the layers separated, the organic phase washed with 1N HCl (125 mL), brine, dried over MgSO4, filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2) eluting with an EtOAc-Heptane gradient to afford 13.5 g of compound 361-A as a tan powder. 1H-NMR (DMSO-d6) δ: 6.89 (s, 1H), 7.33-7.20 (m, 2H), 7.75-7.64 (m, 3H), 7.84-7.76 (m, 3H), 11.30 (s, 1H); MS: m/z 366.1 (M-H)−.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude residue partitioned between EtOAc (500 mL) and 1N HCl (250 mL)
  3. customthe layers separated
  4. washthe organic phase washed with 1N HCl (125 mL), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude residue was purified by flash column chromatography (SiO2)
  9. washeluting with an EtOAc-Heptane gradient

Sources & evidence

ORD record
ord-9e15d4901d7b4ecab209e12ca64ae542
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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