Tosylmethyl isocyanide → 1H-Imidazole, 1,5-diphenyl-

HRID 1023843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023843
[CH:1](=[N:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S([CH2:25][N+:26]#[C-:27])(=O)=O)=CC=1.C(O[Na])(C)(C)C>C1COCC1>[C:9]1([N:8]2[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:27][N:26]=[CH:25]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 161915Tosylmethyl isocyanideHCID 178418730sodium 2-methylpropan-2-olateHCID 178482110HCID 178482110, Verbindung

Produkt 1

HCID 37706691H-Imidazole, 1,5-diphenyl-Ausbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (E)-N-benzylideneaniline (1.0 mmol) in THF (5 mL) was added TOSMIC (1.1 mmol) and t-BuONa (2.2 mmol). The solution was allowed to stir at room temperature for 5 days. The solvent was evaporated under reduced pressure and the crude product was absorbed on silica gel. After purification by flash column chromatography on silica gel the desired product was obtained in 18% yield. 1H NMR: 7.10-7.16 (m, 2H), 7.16-7.23 (m, 2H), 7.23-7.31 (m, 4H), 7.36-7.42 (m, 3H), 7.73 (s, 1H)

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude product was absorbed on silica gel
  3. customAfter purification by flash column chromatography on silica gel the desired product
  4. customwas obtained in 18% yield

Quellen und Nachweise

ORD-Eintrag
ord-8431b24b409744afb48f099add971d42
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722720B2

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