Diisopropylaniline → HCID 178422447, compound

HRID 539462Notes

Reaction equation

HRID 539462 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C[Al](C)C.[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[C:22]#[N:23].ClCCl.CO>C1(C)C=CC=CC=1.CCCCCC>[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[C:22](=[NH:23])[NH:6][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:11]([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 32484DiisopropylanilineHCID 145678583-Bromo-5-methylbenzonitrileHCID 16682925TrimethylaluminumHCID 21226129Dichloromethane methanol

Product 1

HCID 178422447HCID 178422447, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

To a 250 mL 3-neck round bottom flask was added 2,6-diisopropylaniline (2.365 g, 13.34 mmol) and 70 mL toluene. The solution was cooled in an ice bath under nitrogen and trimethylaluminum (2.0 M in toluene, 9.34 mL, 18.68 mmol) was added dropwise via dropping funnel. The reaction mixture was stirred at room temperature for 2 hours. Next, 3-bromo-5-methylbenzonitrile (3.4 g, 17.34 mmol) in 30 mL toluene was added and the reaction mixture was heated to 70° C. overnight under nitrogen. The reaction mixture was cooled in an ice bath and was poured onto a stirring slurry of silica gel in 2:1 dichloromethane/methanol (v/v). The silica gel was filtered off and washed with dichloromethane and methanol. The filtrate was evaporated leaving a solid. Hexane was added to the solvent and the solid was filtered off and washed with hexane (2.92 g, 59%).

Workup

  1. temperatureThe solution was cooled in an ice bath under nitrogen
  2. temperaturethe reaction mixture was heated to 70° C. overnight under nitrogen
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. filtrationThe silica gel was filtered off
  5. washwashed with dichloromethane and methanol
  6. customThe filtrate was evaporated
  7. customleaving a solid
  8. filtrationthe solid was filtered off
  9. washwashed with hexane (2.92 g, 59%)

Sources & evidence

ORD record
ord-1d81eecd64a64bf7aca809b9aec5dae4
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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