Methyl iodide → N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

HRID 2259176

Reaktionsgleichung

Reaktionsgleichung von HRID 2259176
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].CI.[CH3:16]C(C)([O-])C.[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:16])[CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 19693846N-(tert-Butyl)-1H-pyrrole-3-sulfonamideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 19693811N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of N-(1,1-dimethylethyl)-1H-pyrrole-3-sulfonamide 9 g (0.044 mol) in 90 mL N,N-dimethylforamide was cooled to 15° C. under a nitrogen atmosphere. To this was added 3.2 mL (0.053 mol) of methyl iodide followed by 5.43 g (0.048 mol) of potassium t-butoxide. The mixture was warmed at ca. 60° C. for 2 hours then allowed to cool to room temperature and stirred for ca. 2 hours. The reaction mixture was diluted with ethyl acetate, washed three times with 1N HCl, once with brine, dried (MgSO4) and evaporated to an oily solid which was triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134°-135° C. 1H NMR (CDCl3, 200 MHz.) δ: 7.11(s,1H), 6.59(d,1H), 6.41(d,1H), 4.32(bs,1H), 3.67(s,3H), 1.26(s,9H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washwashed three times with 1N HCl
  3. dry with materialonce with brine, dried (MgSO4)
  4. customevaporated to an oily solid which
  5. customwas triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134°-135° C

Quellen und Nachweise

ORD-Eintrag
ord-2958c153c3924c6abfce5f1225a2a15a
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05472933

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