Cesium carbonate → 1-(4-methoxy-benzyl)-1H-tetrazol-5-ylamine

HRID 1514798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514798
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1>CN(C=O)C.CCOC(C)=O>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:3]2[C:2]([NH2:1])=[N:6][N:5]=[N:4]2)=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178509299HCID 178509299, Verbindung

Produkt 1

HCID 240234561-(4-methoxy-benzyl)-1H-tetrazol-5-ylamineAusbeute 17,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of 5-amino-1H-tetrazole (1.50 g, 17.6 mmol) in DMF (30 mL) were added Cs2CO3 (8.62 g, 26.4 mmol) and PMBCl (2.90 g, 18.5 mmol). After stirred at 60° C. for 3 hours, the reaction mixture was cooled to room temperature and diluted with EtOAc. The mixture was washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was diluted with DCM and the resulted precipitate was collected by filtration to give 1-(4-methoxy-benzyl)-1H-tetrazol-5-ylamine (0.625 g). 1H NMR (400 MHz, DMSO-d6) δ 3.73 (s, 3H), 5.27 (s, 2H), 6.78 (s, 2H), 6.92 (d, 2H, J=8.8 Hz), 7.21 (d, 2H, J=8.8 Hz).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washThe mixture was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with DCM
  6. filtrationthe resulted precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-902874a657c14aeb94b1460367ac6b3a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222286B2

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