Benzenesulfonyl chloride → HCID 66924714, compound

HRID 554275Notes

Reaction equation

HRID 554275 reaction equation
[Cl:1][C:2]1[NH:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([F:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].C1OCCOCCOCCOCCOC1.[C:36]1([S:42](Cl)(=[O:44])=[O:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]([S:42]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:44])=[O:43])[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([F:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 66924730HCID 66924730, compound

Product 1

HCID 66924714HCID 66924714, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (60 mL) of ethyl 2-chloro-4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate (330 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 296 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (1.63 g) was added dropwise and the mixture was stirred for 30 min. Benzenesulfonyl chloride (1.13 g) was added, and the mixture was further stirred for 120 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→8:2) to give the title compound as a pale-yellow oil (yield 260 mg, 52%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was further stirred for 120 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→8:2)

Sources & evidence

ORD record
ord-a7d3e2c089d841f08d2611f77ab7d690
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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