Lithium iodide → 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylic acid

HRID 59727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59727
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[C:18]([O:20]C)=[O:19])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[I-].[Li+]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[C:18]([OH:20])=[O:19])(=[O:11])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 66321Lithium iodideHCID 86703835methyl 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 867038341-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylic acidAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of methyl 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylate (Int. 4) (550 mg, 1.773 mmol) in pyridine (25 ml), lithium iodide (1661 mg, 12.41 mmol) was added and the resulting mixture was refluxed for 8 hours. The solution was concentrated under vacuum and the crude was dissolved in DCM (150 ml) and washed with 1N HCl (50 ml×2) and then with brine (50 ml); the organic layer was dried over sodium sulfate and the solvent was removed affording 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylic acid (Int. 5) (433 mg, 1.462 mmol).

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 8 hours
  2. concentrationThe solution was concentrated under vacuum
  3. dissolutionthe crude was dissolved in DCM (150 ml)
  4. washwashed with 1N HCl (50 ml×2)
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-28c544d32ed047e4b1cf1ee63257ed24
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440954B2

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