Sulfuric Acid → N-[(3-Bromophenyl)(phenyl)methylene]-2,6-diisopropylaniline

HRID 45452

Reaktionsgleichung

Reaktionsgleichung von HRID 45452
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH:5]=[CH:6][CH:7]=1.[Si](OCC)(OCC)(OCC)OCC.[CH:29]([C:32]1[CH:38]=[CH:37][CH:36]=[C:35]([CH:39]([CH3:41])[CH3:40])[C:33]=1[NH2:34])([CH3:31])[CH3:30].OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:34][C:33]2[C:35]([CH:39]([CH3:40])[CH3:41])=[CH:36][CH:37]=[CH:38][C:32]=2[CH:29]([CH3:31])[CH3:30])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 1118Sulfuric AcidHCID 6517TetraethoxysilaneHCID 32484DiisopropylanilineHCID 705483-Bromobenzophenone

Produkt 1

HCID 58238566N-[(3-Bromophenyl)(phenyl)methylene]-2,6-diisopropylanilineAusbeute 84 %

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

In 25 mL Claisens flask in an argon atmosphere, a mixture of 5.22 g (20.0 mmol) of 16, 5.00 g (24.0 mmol) of Si(OEt)4, and 3.90 g (22.0 mmol) of 2,6-diisopropylaniline was heated to 170° C., and then 0.13 mL of 96% H2SO4 was added. This mixture was stirred at this temperature for 50 hr, and the formed ethanol was slowly distilled off. Later, 300 mL of cold water was added, and the product was extracted with 2×70 mL of diethyl ether. The combined extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 100:1, vol.). This procedure gave 7.06 g (84%) of the title product 17.

Aufarbeitung

  1. distillationthe formed ethanol was slowly distilled off
  2. additionLater, 300 mL of cold water was added
  3. extractionthe product was extracted with 2×70 mL of diethyl ether
  4. extractionThe combined extract
  5. dry with materialwas dried over K2CO3
  6. customevaporated to dryness
  7. customThe product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 100:1, vol.)

Quellen und Nachweise

ORD-Eintrag
ord-0e303e463c954cfc95695fabddd0c80e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541522B2

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