Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amide → Benzo[b]thiophene-2-sulfonic acid

HRID 730206Notes

Reaction equation

HRID 730206 reaction equation
NC1C=CC=CC=1N[S:9]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)(=[O:11])=[O:10].C[O:22]C1C=CC(S(C(C)C)(=O)=O)=CC=1S(Cl)(=O)=O>C(Cl)Cl.N1C=CC=CC=1>[S:16]1[C:12]([S:9]([OH:10])(=[O:11])=[O:22])=[CH:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]1=2

Participants

5

Reactant 2

HCID 86240018Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amideHCID 862400252-Methoxy-5-(propane-2-sulfonyl)benzenesulfonyl chloride

Product 1

HCID 18176377Benzo[b]thiophene-2-sulfonic acidYield 214.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)-amide (1 mmol) (prepared as in example 1) in DCM (2 mL) and pyridine (2 mL), 2-methoxy-5-(propane-2-sulfonyl)benzenesulfonyl chloride (1.1 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (10 mL). The organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL) and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to obtain 460 mg of benzo[b]thiophene-2-sulfonic acid {2-[2-methoxy-5-(propane-2 sulfonyl) benzenesulfonylamino]phenyl-amide. Tr 1.09 min; MS: 581.4 (M+1)+. 1H NMR (DMSO-d6, 400 MHz): δ 0.97 (d, 6H), 3.58 (m, 1H), 4.02 (s, 3H), 6.84 (dd, 1H), 7.96 (td, 1H), 7.10 (td, 1H), 7.23 (dd, 1H), 7.44-7.54 (m, 3H), 7.86 (d, 1H), 7.90 (s, 1H), 7.96 (d, 1H), 8.03 (dd, 2H), 9.22 (bs, 1H), 9.79 (s, 1H) ppm.

Workup

  1. washThe organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL) and brine (10 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM/EtOAc

Sources & evidence

ORD record
ord-2c6e626166434788b43f5928cd7ee125
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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