Sulfuric Acid → HCID 86041032, compound

HRID 1296078Notes

Reaction equation

HRID 1296078 reaction equation
C(O[Si](OCC)(OCC)OCC)C.S(=O)(=O)(O)O.[Br:19][C:20]1[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[C:23]([NH2:24])=[C:22]([CH:30]([CH3:32])[CH3:31])[CH:21]=1.[C:33]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[OH-].[K+]>>[C:34]1([C:33]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[N:24][C:23]2[C:25]([CH:27]([CH3:28])[CH3:29])=[CH:26][C:20]([Br:19])=[CH:21][C:22]=2[CH:30]([CH3:32])[CH3:31])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 3102BenzophenoneHCID 6517TetraethoxysilaneHCID 14797Potassium HydroxideHCID 117801144-Bromo-2,6-diisopropylaniline

Product 1

HCID 86041032HCID 86041032, compoundYield 77%

Conditions

Temperature
160 °C

Procedure

40.7 g (0.195 mol) of tetraethoxysilane and 0.5 mL of sulfuric acid were added to a flask equipped with a distiller, containing 43.9 g (0.169 mol) of 4-bromo-2,6-diisopropylaniline and 24.8 g (0.130 mol) of benzophenone under a nitrogen atmosphere. The mixture was reacted by heating at 160° C. for 2 days while removing formed ethanol using the distiller. After the reaction, the resultant product was cooled to room temperature. Then, 200 mL of 1.0 M aqueous solution of potassium hydroxide was added to the resultant product and stirred for 10 minutes to obtain yellow precipitates. The obtained precipitates were filtered off and dissolved in 300 mL of ethyl acetate, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain a yellow solid. Then, the yellow solid was recrystallized in hexane at −20° C. to obtain 42 g of N-diphenylmethylene-2,6-diisopropyl-4-bromoaniline compound.

Workup

  1. customequipped with a distiller
  2. customThe mixture was reacted
  3. customwhile removing
  4. customformed ethanol using the distiller
  5. customAfter the reaction
  6. customto obtain yellow precipitates
  7. customThe obtained precipitates
  8. filtrationwere filtered off
  9. dissolutiondissolved in 300 mL of ethyl acetate
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customto obtain a yellow solid
  13. customThen, the yellow solid was recrystallized in hexane at −20° C.

Sources & evidence

ORD record
ord-776327b8ccd34d389d74d57c5e9938ab
Source dataset
uspto-grants-2007_07
Patent number
US07244805B2

Reaction notes

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