Potassium Iodide → methyl 5-(diphenylmethyl)-2H-tetrazole-2-nonanoate

HRID 1031942

Reaktionsgleichung

Reaktionsgleichung von HRID 1031942
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C(OCC)C.CN(C=O)C>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[N:9]=[N:10][N:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[N:12]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 554142Methyl 9-bromononanoateHCID 178420203HCID 178420203, Verbindung

Produkt 1

HCID 15068037methyl 5-(diphenylmethyl)-2H-tetrazole-2-nonanoateAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-(diphenylmethyl)-1H-tetrazole (5 g, 21 mmol) obtained according to J. W. Cusic, U.S. Pat. No. 3,155,666, methyl 9-bromononanoate (5.84 g, 23 mmol), potassium carbonate (3.50 g, 25 mmol), potassium iodide (catalytic quantity) and DMF (75 mL) was stirred at 110° C. for 15 minutes. The mixture was cooled, diluted with water and extracted three times with diethyl ether. The combined extracts were washed three times with water, dried over sodium sulfate and concentrated in vacuo to give an oil. Chromatography on a column of silica gel using a mixture of hexanes and diethyl ether (1:1) as eluent gave methyl 5-(diphenylmethyl)-2H-tetrazole-2-nonanoate (6.50 g, 75%).

Aufarbeitung

  1. customobtained
  2. temperatureThe mixture was cooled
  3. extractionextracted three times with diethyl ether
  4. washThe combined extracts were washed three times with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-791f02d69c1347a2a90aeaf0b496b199
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04956376

Verknüpfte Notizen

Wird geladen…