2-Methoxyethylamine → 4-amino-N-(2-methoxyethyl)benzene-1-sulfonamide

HRID 495372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 495372
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[S:6](F)(=[O:15])([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)=[O:7].C(N(CC)CC)C>C(O)CCC>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6]([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:15])=[O:7]

Komponenten

5

Edukt 3

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 668234-Aminobenzenesulfonyl fluoride

Produkt 1

HCID 167819184-amino-N-(2-methoxyethyl)benzene-1-sulfonamideAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 2-methoxyethylamine (859 mg, 11.4 mmol), sulphanilyl fluoride (1.0 g, 5.71 mmol) and triethylamine (1.72 g, 22.9 mmol) in 1-butanol (15 ml) was heated at reflux for 18 hours. The mixture was allowed to cool and the volatiles were removed by evaporation. The residue was purified by chromatography eluting with ethyl acetate/hexane (50:50) increasing in polarity to (70:30) to give the title compound (860 mg, 65%). NMR: 2.78 (q, 2H), 3.15 (s, 3H), 3.25 (t, 2H), 5.87 (s, 2H), 6.58 (d, 2H), 7.10 (t, 1H), 7.40 (d, 2H); m/z 231.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureto cool
  4. customthe volatiles were removed by evaporation
  5. customThe residue was purified by chromatography
  6. washeluting with ethyl acetate/hexane (50:50)
  7. temperatureincreasing in polarity to (70:30)

Quellen und Nachweise

ORD-Eintrag
ord-d69b87f4c03c41eb9db78e5e4ada6c17
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939872B2

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