Diethyl Ether → HCID 67215554, compound

HRID 2421449Notes

Reaction equation

HRID 2421449 reaction equation
C[Mg+].[Br-].CCOCC.[CH:9]([NH:12][CH:13]([CH3:15])[CH3:14])([CH3:11])[CH3:10].[C:16]1([CH3:24])[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=1>C1(C)C=CC=CC=1>[CH:9]([N:12]([CH:13]([CH3:15])[CH3:14])[C:22]([C:17]1[C:16]([CH3:24])=[CH:21][CH:20]=[CH:19][CH:18]=1)=[NH:23])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7912DiisopropylamineHCID 107212-MethylbenzonitrileHCID 178418689HCID 178418689, compound

Product 1

HCID 67215554HCID 67215554, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of MeMgBr in ether (12.9 mL, 3.0 M, 38.7 mmol) was added to a solution of diisopropylamine (3.91 g, 38.7 mmol) in toluene (60 mL) at 50° C. The mixture was stirred for 1 h and a white precipitate formed. Next, the mixture was cooled to 0° C. and tolunitrile (4.53 g, 38.7 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 16 h subsequently. The mixture was quenched with water (100 mL). The organic phase was separated from the aqueous phase and the latter was extracted with diethylether (150 mL) twice. The combined organic phases were dried over Na2SO4, filtered and the solvents were removed under reduced pressure giving a sticky residue. This residue was triturated with ligroin giving 4.40 g (52%) pure product.

Workup

  1. customa white precipitate formed
  2. temperatureto warm to room temperature
  3. stirringstirred for 16 h subsequently
  4. customThe mixture was quenched with water (100 mL)
  5. customThe organic phase was separated from the aqueous phase
  6. extractionthe latter was extracted with diethylether (150 mL) twice
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customgiving a sticky residue
  11. customThis residue was triturated with ligroin giving 4.40 g (52%) pure product

Sources & evidence

ORD record
ord-0201ef0769c14625bb6b7d9e0536f371
Source dataset
uspto-grants-2011_06
Patent number
US07956140B2

Reaction notes

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