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

HRID 45452

反応式

HRID 45452 の反応式
[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

参加物

5

反応物 4

HCID 1118Sulfuric AcidHCID 6517TetraethoxysilaneHCID 32484DiisopropylanilineHCID 705483-Bromobenzophenone

生成物 1

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

反応条件

温度
170 °C

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-0e303e463c954cfc95695fabddd0c80e
出典データセット
uspto-grants-2013_09
特許番号
US08541522B2

関連ノート

読み込み中…