Dimethylformamide → HCID 54384707, Verbindung

HRID 1004365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1004365
[CH3:1][N:2]([CH3:5])C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:12][O:13][N:14]=[C:15]([C:32]1[NH:36][N:35]=[N:34][N:33]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31].S(OC)(OC)(=O)=O>CCOCC>[CH3:12][O:13][N:14]=[C:15]([C:32]1[N:36]([CH3:1])[N:35]=[N:34][N:33]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31].[CH3:12][O:13][N:14]=[C:15]([C:32]1[N:33]=[N:34][N:2]([CH3:5])[N:36]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178502648HCID 178502648, Verbindung

Produkt 2

HCID 54384707HCID 54384707, VerbindungAusbeute 37,9 %HCID 54527829HCID 54527829, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

N,N-Dimethylformamide (3 ml) and potassium carbonate (0.33 g, 2.4 mmol) were added to 2-(2,5-dimethylphenoxymethyl)phenyl 1H-tetrazol-5-yl ketone O-methyloxime (0.40 g, 1.2 mmol), and the mixture was stirred at room temperature for 5 minutes. Then, dimethyl sulfate (0.23 g, 1.8 mmol) was added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, ether (150 ml) was added, and the mixture was washed with brine (50 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl 1-methyl-1H-tetrazol-5-yl ketone O-methyloxime as colorless crystals (0.16 g, 37.9%) [mp. 115.5-116.5° C.; 1H-NMR(CDCl3) δ ppm: 1.97(3H,s), 2.26(3H,s), 4.06(3H,s), 4.13(3H,s), 4.89(2H,s), 6.50(1H,s), 6.65(1H,d,J=7.9), 6.97(1H,d,J=7.9), 7.34-7.58(4H,m)] and 2-(2,5-dimethylphenoxymethyl)phenyl 2-methyl-2H-tetrazol-5-yl ketone O-methyloxime as colorless crystals (0.08 g, 19.0%) [mp. 131-132° C.; 1H-NMR(CDCl3) δ ppm: 2.12(3H,s), 2.24(3H,s), 4.09(3H,s), 4.34(3H,s), 4.96(2H,s), 6.54(1H,s), 6.64(1H,d,J=7.9), 6.98(1H,d,J=7.3), 7.29-7.53(3H,m), 7.69(1H,d,J=7.3)].

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. additionwas added
  4. washthe mixture was washed with brine (50 ml) twice
  5. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  8. customrecrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6d0af137a7f84df0be8ba3da7337a88d
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06048885

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