Water → HCID 178509593, compound

HRID 1254026Notes

Reaction equation

HRID 1254026 reaction equation
[C:1]1([C:7](=[NH:9])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:11][C:12]([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)=O.C(=O)(O)[O-].[Na+].O>C1COCC1>[C:1]1([C:7]2[NH:9][CH:11]=[C:12]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2332BenzamidineHCID 986544-(Bromoacetyl)benzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 178509593HCID 178509593, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzenecarboximidamide (2.9 g, 24 mmol), 4-bromoacetylbenzonitrile (5 g, 22 mmol), and sodium bicarbonate (1.8 g, 22 mmol) were suspended in 70 mL of THF and 10 mL of water and heated at reflux overnight. The reaction mixture was cooled rt, and partially concentrated. An additional 10 mL of water was added, and the resulting suspension was stirred at 50-60° C. for 30 min. The mixture was cooled with an ice-water bath and the precipitate was collected by filtration, rinsed with two 10-mL portions of water, and air-dried. The solid material was stirred with 15 mL of EtOAc and 15 mL of hexanes, and was again collected by filtration, and dried to give 4-(2-phenyl-1H-imidazol-4-yl)benzonitrile. LCMS: min [M+1]=246.

Workup

  1. temperatureat reflux overnight
  2. concentrationpartially concentrated
  3. additionAn additional 10 mL of water was added
  4. temperatureThe mixture was cooled with an ice-water bath
  5. filtrationthe precipitate was collected by filtration
  6. washrinsed with two 10-mL portions of water
  7. customair-dried
  8. stirringThe solid material was stirred with 15 mL of EtOAc and 15 mL of hexanes
  9. filtrationwas again collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-25a942db3f3e4f068f63efdc01f86b21
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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