Hydrochloric Acid → HCID 178520358, Verbindung

HRID 1795107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795107
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH:23]1[CH:27]=[C:26]([CH2:28][C:29]([NH:31][NH2:32])=[O:30])[N:25]=[CH:24]1.Cl>C(O)C.O1CCOCC1>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:19]=[N:32]/[NH:31][C:29](=[O:30])[CH2:28][C:26]2[N:25]=[CH:24][NH:23][CH:27]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 221856712-Formylphenyl 4-(trifluoromethyl)benzenesulfonateHCID 178514425HCID 178514425, Verbindung

Produkt 1

HCID 178520358HCID 178520358, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-formylphenyl 4-(trifluoromethyl)benzenesulfonate (6.5 g, 19.7 mmol) in ethanol (100 ml) is added to a solution of 4-imidazoleacetic acid hydrazide (18 mmol) in ethanol (200 mL). A catalytic amount of HCl in dioxane (3 mL) is added and the mixture is stirred at room temperature overnight. The precipitate that forms is removed by filtration. The filtrate is concentrated and chromatographed on silica eluting with 5% (2M ammonia in methanol)/CH2Cl2 to give 2-((E)-{2-[2-(1H-imidazol-4-yl)acetyl]hydrazono}methyl)phenyl 4-(trifluoromethyl)benzenesulfonate as a white solid. The yield is 3.1 g, 38%. 1H NMR (400 MHz, DMSO) d 11.94 (s, 1H), 11.48 (2s, 1H), 8.02 (m, 6H), 7.21 (m, 5H), 3.64 (2 s, 2H). ESI+ for C19H15F3N4O4S, m/z 453, (M+H)+.

Aufarbeitung

  1. customThe precipitate that forms is removed by filtration
  2. concentrationThe filtrate is concentrated
  3. customchromatographed on silica eluting with 5% (2M ammonia in methanol)/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-d3f51939e4d54dccb9094c23f29cec9a
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026339B2

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