4-Cyanobenzenesulfonyl chloride → N-(Benzo[b]thiophen-2-yl)-4-cyanobenzenesulfonamide

HRID 57174

Reaction equation

HRID 57174 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.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1)#[N:13]>N1C=CC=CC=1.C(Cl)Cl>[S:2]1[C:6]([NH:7][S:20]([C:17]2[CH:16]=[CH:15][C:14]([C:12]#[N:13])=[CH:19][CH:18]=2)(=[O:22])=[O:21])=[CH:5][C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]1=2

Participants

5

Reactant 2

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 66906726Benzo[b]thiophen-2-amine hydrochloride

Product 1

HCID 57920354N-(Benzo[b]thiophen-2-yl)-4-cyanobenzenesulfonamideYield 77.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 1-C (0.927 g, 5.0 mmol) in pyridine (10 mL) and methylene chloride (5 mL), cooled on an ice bath, was added 4-cyanobenzene-1-sulfonyl chloride (1.01 g, 5.0 mmol) portion-wise over 3 min. The reaction was allowed to warm slowly to ambient temperature and allowed to stir for 72 h. The reaction mixture was concentrated under reduced pressure, the crude residue was partitioned between EtOAc (100 mL) and 1N HCl (25 mL), the layers separated, the organic phase washed with brine (25 mL), 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 1.22 g of compound 389-A as a tan-brown powder. 1H-NMR (DMSO-d6): δ 6.91 (s, 1H), 7.33-7.21 (m, 2H), 7.69-7.64 (m, 1H), 7.82-7.76 (m, 1H), 7.99-7.93 (m, 2H), 8.11-8.05 (m, 2H), 11.49 (br s, 1H); MS: m/z 313.1 (M-H)−.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude residue was partitioned between EtOAc (100 mL) and 1N HCl (25 mL)
  3. customthe layers separated
  4. washthe organic phase washed with brine (25 mL)
  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-39174e62266b4029b30fa917c06b66f9
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Linked notes

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