Sodium Methoxide → Benzo[b]thiophene-2-sulfonic acid [2-(2-methoxy-5-trifluoromethyl-benzenesulfonylamino)phenyl]-amide

HRID 730221Notes

Reaction equation

HRID 730221 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][S:23]([C:26]1[S:30][C:29]2[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=2[CH:27]=1)(=[O:25])=[O:24])(=[O:14])=[O:13].[CH3:35][O-:36].[Na+]>O1CCOCC1.CCOC(C)=O>[CH3:35][O:36][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][S:23]([C:26]1[S:30][C:29]2[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=2[CH:27]=1)(=[O:25])=[O:24])(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 11599202Benzo[b]thiophene-2-sulfonic acid [2-(2-chloro-5-trifluoromethylbenzenesulfonylamino)phenyl]-amide

Product 1

HCID 11649592Benzo[b]thiophene-2-sulfonic acid [2-(2-methoxy-5-trifluoromethyl-benzenesulfonylamino)phenyl]-amideYield 75.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of benzo[b]thiophene-2-sulfonic acid [2-(2-chloro-5-trifluoromethylbenzenesulfonylamino)phenyl]-amide (0.5 mmol) in dioxane (5 mL), solid sodium methoxide (2 mmol) was added in one portion and the resulting reaction mixture was then heated to reflux for ca. 4 h. After the completion of the reaction, the reaction mixture was cooled to RT and concentrated in vacuo. The residue obtained was redissolved in EtOAc (10 mL) and was washed with 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 204 mg of benzo[b]thiophene-2-sulfonic acid [2-(2-methoxy-5-trifluoromethyl-benzenesulfonylamino)phenyl]-amide. LC: Tr 1.20 min; MS: 544.1 (M+1)+.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureto reflux for ca. 4 h
  4. customAfter the completion of the reaction
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. washwas washed with water (10 mL) and brine (10 mL)
  8. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe residue obtained
  11. customwas purified by flash column chromatography
  12. washeluting with DCM/EtOAc

Sources & evidence

ORD record
ord-24aa34e0f0314f6493eeb075e90323f6
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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