HCID 58107424, compound → HCID 58107463, compound

HRID 1810190Notes

Reaction equation

HRID 1810190 reaction equation
C1(S([N:10]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([Cl:27])=[C:21]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:22]=3)=[O:16])=[CH:11]2)(=O)=O)C=CC=CC=1>CO.[OH-].[Na+]>[Cl:27][C:20]1[CH:19]=[CH:18][C:17]([C:15]([C:12]2[CH:13]=[CH:14][NH:10][CH:11]=2)=[O:16])=[CH:22][C:21]=1[S:23]([NH2:26])(=[O:24])=[O:25]

Participants

4

Reactant 1

HCID 58107424HCID 58107424, compound

Product 1

HCID 58107463HCID 58107463, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-(1-Benzenesulfonyl-1H-pyrrole-3-carbonyl)-2-chloro-benzenesulfonamide (0.1 g, 0.23 mmol) is dissolved in 3 mL of 2:1 (v:v) mixture of methanol and 5 N aqueous sodium hydroxide and heated at reflux for 20 minutes then the reaction mixture is allowed to cool down and the organic solvent is removed in vacuo. The aqueous solution is acidified with 5 N HCl to pH 3, thoroughly extracted with ethyl acetate, then the combined organic extracts are washed with water, a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Recrystallization from ethyl acetate/methylene chloride provides 43 mg (66%) of the title compound as a white solid. 1H NMR (DMSO): δ 11.70 (s, 1H), 8.70 (m, 1H), 8.00 (m, 1H), 7.80 (m, 3H), 7.50 (m, 1H), 7.00 (m, 1H), 6.60 (m, 1H). MS (m/z): 285 (M+1) Analytics calculated For C11H9N2ClO3S: C, 46.40; H, 3.19; N, 9.84. Found: C, 45.84; H, 2.90; N, 9.41.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 minutes
  3. temperatureto cool down
  4. customthe organic solvent is removed in vacuo
  5. extractionthoroughly extracted with ethyl acetate
  6. washthe combined organic extracts are washed with water
  7. dry with materiala saturated sodium chloride solution, dried with magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customRecrystallization from ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-de2a9b1b198a47fbb339707dc50d0202
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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