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Sodium Iodide → 2-(tert-Butyldimethylsilyloxymethyl)-5-(N-triphenylmethyltetrazol-5-yl)methyl-10,11-dihydro-5H-dibenz[b,f]azepine

HRID 1768659
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1768659
[Si:1]([O:8][CH2:9][C:10]1[CH:24]=[CH:23][C:13]2[NH:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[CH2:17][CH2:18][C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[CH2:26][C:27]1[N:31]([C:32]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:30]=[N:29][N:28]=1.[I-].[Na+].[H-].[Na+]>CN(C=O)C>[Si:1]([O:8][CH2:9][C:10]1[CH:24]=[CH:23][C:13]2[N:14]([CH2:26][C:27]3[N:31]([C:32]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:30]=[N:29][N:28]=3)[C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[CH2:17][CH2:18][C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 234980175-(Chloromethyl)-1-(triphenylmethyl)-1H-tetrazoleHCID 53676808HCID 53676808, Verbindung

Produkt 1

HCID 199708572-(tert-Butyldimethylsilyloxymethyl)-5-(N-triphenylmethyltetrazol-5-yl)methyl-10,11-dihydro-5H-dibenz[b,f]azepine

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1.3 g of Compound 31-2b, 2.0 g of 5-chloromethyl-N-triphenylmethyltetrazole, 0.6 g of sodium iodide, 0.2 g of sodium hydride (60% oily) and 50 ml of DMF was stirred at 80° C. for 15 hours. The solvent was distilled off under reduced pressure, and the residue was diluted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (10/1)] to give 1.05 g of an oily substance containing the desired compound.

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (10/1)]
  7. customto give 1.05 g of an oily substance

Quellen und Nachweise

ORD-Eintrag
ord-c2da9879ef724f9e8cb3730a4110b43a
Quelldatensatz
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05378701

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