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Triphenylcarbinol → 2-(1-Trityl-1H-imidazol-4-yl)-benzonitrile

HRID 1795257
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1795257
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1.[Cu][C:33]#[N:34].C(O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CN(C)C=O.C1(C)C=CC=CC=1>[C:13]([N:11]1[CH:12]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:33]#[N:34])[N:9]=[CH:10]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6457TriphenylcarbinolHCID 221851434-(2-bromophenyl)-1-trityl-1H-imidazoleHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 221851592-(1-Trityl-1H-imidazol-4-yl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-(2-bromo-phenyl)-1-trityl-1H-imidazole (73.0 g, 163.3 mmol) in dimethylformamide (500 ml) was added copper (I) cyanide (17.5 g, 195.9 mmol). The reaction was heated to ˜80° C. under nitrogen for 14 h. After cooling to about 50° C., the reaction was diluted with toluene (ca. 300 ml) and slowly poured onto ammonium hydroxide (3N, 1.5 L) while stirring vigorously. The mixture was stirred for 40 min and then filtered in vacuo over a bed of celite (slow filtration, required ˜2 h). The phases were separated and the organic layer was washed with brine (75 ml×3) and dried (sodium sulfate). Concentration of the solvent afforded a light brown solid. The crude product contains ˜10–15% of trityl alcohol (by HPLC) and was used without further purification in the subsequent step.

Aufarbeitung

  1. temperatureAfter cooling to about 50° C.
  2. additionslowly poured onto ammonium hydroxide (3N, 1.5 L)
  3. stirringThe mixture was stirred for 40 min
  4. filtrationfiltered in vacuo over a bed of celite (
  5. filtrationslow filtration
  6. custom˜2 h
  7. customThe phases were separated
  8. washthe organic layer was washed with brine (75 ml×3)
  9. dry with materialdried (sodium sulfate)
  10. customConcentration of the solvent afforded a light brown solid
  11. customwas used without further purification in the subsequent step

Quellen und Nachweise

ORD-Eintrag
ord-6268f68576ce443bb9613929eb45e039
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07026324B2

Notizen zur Reaktion

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