Sulfuric Acid → HCID 58238597, compound

HRID 45481Notes

Reaction equation

HRID 45481 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=O)[CH:5]=[CH:6][CH:7]=1.[Si](OCC)(OCC)(OCC)OCC.[CH:30]([C:33]1[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]([CH3:42])[CH3:41])[C:34]=1[NH2:35])([CH3:32])[CH3:31].OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[N:35][C:34]2[C:36]([CH:40]([CH3:41])[CH3:42])=[CH:37][CH:38]=[CH:39][C:33]=2[CH:30]([CH3:32])[CH3:31])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6517TetraethoxysilaneHCID 32484DiisopropylanilineHCID 2757054(3-Bromophenyl)(4-methylphenyl)methanone

Product 1

HCID 58238597HCID 58238597, compoundYield 84%

Conditions

Temperature
170 °C

Procedure

In 50 mL Claisens flask in an argon atmosphere, a mixture of 9.63 g (35.0 mmol) of 40, 8.75 g (42.0 mmol) of Si(OEt)4, and 6.83 g (38.5 mmol) of 2,6-diisopropylaniline was heated to 170° C., and then 0.23 mL of 96% H2SO4 was added. This mixture was stirred at this temperature for 55 hr, and the formed ethanol was slowly distilled off. Further on, 300 mL of cold water was added, and the product was extracted with 2×100 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.) to give 12.7 g (84%) of the title product.

Workup

  1. distillationthe formed ethanol was slowly distilled off
  2. additionFurther on, 300 mL of cold water was added
  3. extractionthe product was extracted with 2×100 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.)

Sources & evidence

ORD record
ord-3491685b67104c8fb37adb08498041f3
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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