Trifluoroacetic acid → 2-[(Methoxyimino)methyl]-1-methyl-1H-pyrrole-3-sulfonamide

HRID 2259186

Reaktionsgleichung

Reaktionsgleichung von HRID 2259186
CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][C:10]=1[CH:14]=[N:15][O:16][CH3:17])(=[O:8])=[O:7])(C)C.[C:18](O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:17][O:16][N:15]=[CH:14][C:10]1[N:11]([CH3:18])[CH:12]=[CH:13][C:9]=1[S:6]([NH2:5])(=[O:7])=[O:8]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 136144806N-(1,1-Dimethylethyl)-2-[(methoxyimino)methyl]-1H-pyrrole-3-sulfonamide

Produkt 1

HCID 541233872-[(Methoxyimino)methyl]-1-methyl-1H-pyrrole-3-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5.74 g (21.9 mmol) of N-(1,1-dimethylethyl)-2-[(methoxyimino)-methyl]-1H-pyrrole-3-sulfonamide in 75 mL methylene chloride under a nitrogen atmosphere was add 75 mL of TFA. The clear orange reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The orange reaction mixture was concentrated in vacuo. Three portions of diethyl ether were added to the residue and removed by evaporation to remove residual TFA, affording 3.49 g of the title compound as a gray solid, m.p. 120°-122° C. 1H NMR (CDCl3, 200 MHz.) δ: 8.43(s,1H), 6.66(d,1H), 6.54(d,1H), 6.1-6.7(bs,2H), 3.96(s,3H), 3.79(s,3H).

Aufarbeitung

  1. concentrationThe orange reaction mixture was concentrated in vacuo
  2. additionThree portions of diethyl ether were added to the residue
  3. customremoved by evaporation
  4. customto remove residual TFA

Quellen und Nachweise

ORD-Eintrag
ord-930b5ef0b22146469e59a8c1895f49b3
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05472933

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