Sulfuric Acid → N-[1-(3-Bromophenyl)ethylidene]-2,6-diisopropylaniline

HRID 45477

반응식

HRID 45477 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[CH:5]=1)=O.[Si](OCC)(OCC)(OCC)OCC.[CH:24]([C:27]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]([CH3:36])[CH3:35])[C:28]=1[NH2:29])([CH3:26])[CH3:25].OS(O)(=O)=O>>[Br:10][C:6]1[CH:5]=[C:4]([C:2](=[N:29][C:28]2[C:30]([CH:34]([CH3:35])[CH3:36])=[CH:31][CH:32]=[CH:33][C:27]=2[CH:24]([CH3:26])[CH3:25])[CH3:1])[CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 6517TetraethoxysilaneHCID 165023'-BromoacetophenoneHCID 32484Diisopropylaniline

생성물 1

HCID 58238584N-[1-(3-Bromophenyl)ethylidene]-2,6-diisopropylaniline수율 88%

반응 조건

온도
170 °C

실험 절차

In 25 mL Claisens flask in an argon atmosphere, a mixture of 3.98 g (20.0 mmol) of 3-bromoacetophenone, 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 0.20 mL of 96% H2SO4 was added. This mixture was stirred at this temperature for 1 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, 50:1, vol.). This procedure gave 6.30 g (88%) of 13.

후처리

  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, 50:1, vol.)

출처 및 근거

ORD 기록
ord-3a7efc57dd0047a28191eb923560f6a5
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541522B2

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