Acetonitrile → HCID 178441581, compound

HRID 2389281Notes

Reaction equation

HRID 2389281 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])=O.[CH3:13][C:14]([C:17]([NH2:19])=[NH:18])([CH3:16])[CH3:15].Cl.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:14]([C:17]1[NH:18][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[C:8]#[N:9])[N:19]=1)([CH3:16])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27358673-(2-Bromoacetyl)benzonitrileHCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)

Product 1

HCID 178441581HCID 178441581, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(2-bromoacetyl)benzonitrile (500 mg, 2.23 mmol), tert-butylcarbamidine hydrochloride (610 mg, 4.46 mmol), potassium carbonate (770 mg, 5.58 mmol), and acetonitrile (10 mL) was refluxed for 1 hour. After the reaction was completed, the mixture was left to cool to room temperature. Then, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure to give 3-(2-tert-butyl-1H-imidazol-4-yl)benzonitrile (500 mg, 2.22 mmol, yield: 99%).

Workup

  1. temperaturewas refluxed for 1 hour
  2. waitthe mixture was left
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1263f457ebee454f90f72b6cd89cd1ec
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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