1,4-Dioxane → N-[2-(4-chlorobenzenesulfonylamino)phenyl]-2-methoxy-5-trifluoromethylbenzenesulfonamide

HRID 730229Notes

Reaction equation

HRID 730229 reaction equation
ClC1C=[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[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])(=[O:14])=[O:13].C[O-].[Na+].O1[CH2:41][CH2:40][O:39][CH2:38]C1>CCOC(C)=O>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([NH:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][S:12]([C:3]2[CH:4]=[C:5]([C:8]([F:10])([F:9])[F:11])[CH:6]=[CH:41][C:40]=2[O:39][CH3:38])(=[O:13])=[O:14])(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 10942334Sodium MethoxideHCID 689490302-chloro-N-[2-(4-chloro-benzenesulfonylamino)phenyl]-5-trifluoromethylbenzenesulfonamide

Product 1

HCID 11634995N-[2-(4-chlorobenzenesulfonylamino)phenyl]-2-methoxy-5-trifluoromethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-N-[2-(4-chloro-benzenesulfonylamino)phenyl]-5-trifluoromethylbenzenesulfonamide (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 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 160 mg of N-[2-(4-chlorobenzenesulfonylamino)phenyl]-2-methoxy-5-trifluoromethylbenzenesulfonamide. LC: Tr 1.22 min; MS: 521.8 (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. washwashed 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-216d5c7c66fe458db8a9916c5d9789f6
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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