1-Phenylsulfonylpyrrole → HCID 58107424, compound

HRID 873661Notes

Reaction equation

HRID 873661 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]=1[S:15](=[O:18])(=[O:17])[NH2:16].[C:19]1([S:25]([N:28]2[CH:32]=[CH:31][CH:30]=[CH:29]2)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[C:19]1([S:25]([N:28]2[CH:29]=[CH:30][C:31]([C:10]([C:9]3[CH:13]=[CH:14][C:6]([Cl:5])=[C:7]([S:15]([NH2:16])(=[O:18])=[O:17])[CH:8]=3)=[O:11])=[CH:32]2)(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 1401461-PhenylsulfonylpyrroleHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 58107424HCID 58107424, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of aluminum chloride (1.89 g, 14 mmol) in methylene chloride (10 mL) is added 4-chloro-3-sulfamoyl-benzoyl chloride (2 g, 7.9 mmol). The reaction mixture is stirred at room temperature for 10 minutes then a solution of 1-benzenesulfonyl-1H-pyrrole (1.13 g, 5.45 mmol) in methylene chloride (3.3 mL) is added. After stirring at room temperature overnight, the reaction is quenched with 6 N HCl and extracted with ethyl acetate three times. The combined organic layers are washed with a saturated sodium chloride solution, dried with magnesium sulfate and concentrated in vacuo. Purification by silica gel chromatography (ethyl acetate/hexane: 2:8) provides 0.6 g (26%) of the title compound as a yellow solid. 1H NMR (DMSO): δ 8.30 (s, 1H), 8.15 (m, 2H), 8.05 (m, 2H), 7.80 (m, 4H), 7.70 (m, 2H), 7.40 (m, 1H), 6.70 (m, 1H).

Workup

  1. stirringAfter stirring at room temperature overnight
  2. customthe reaction is quenched with 6 N HCl
  3. extractionextracted with ethyl acetate three times
  4. washThe combined organic layers are washed with a saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography (ethyl acetate/hexane: 2:8)

Sources & evidence

ORD record
ord-ca0963e4d2734b10989ff2afe205c502
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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