Diisopropylaniline → HCID 178490167, compound

HRID 539453Notes

Reaction equation

HRID 539453 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.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[C:23]#[N:24].ClCCl.CO>C1(C)C=CC=CC=1.CCCCCC>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:23](=[NH:24])[C:22]1[CH:25]=[C:26]([CH3:28])[CH:27]=[C:20]([O:19][CH3:18])[CH:21]=1)([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 32484DiisopropylanilineHCID 16682925TrimethylaluminumHCID 21226129Dichloromethane methanolHCID 219499033-Methoxy-5-methylbenzonitrile

Product 1

HCID 178490167HCID 178490167, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

To a 500 mL 3-neck round bottom flask was added 2,6-diisopropylaniline (4.82 g, 27.2 mmol) and 100 mL toluene. The solution was cooled in an ice bath under nitrogen and trimethylaluminum (2.0 M in toluene, 19 mL, 38.1 mmol) was added dropwise via dropping funnel. The reaction mixture was stirred at room temperature for 2 hours. Next, 3-methoxy-5-methylbenzonitrile (5.20 g, 35.3 mmol) in 50 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 (5.83 g, 66%).

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 (5.83 g, 66%)

Sources & evidence

ORD record
ord-7f6d47c62d814344ba4137b9e8b7adbf
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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