Boron tribromide → HCID 136386016, compound

HRID 2085215Notes

Reaction equation

HRID 2085215 reaction equation
C[O:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH:5]=[C:6]1[N:10]=[C:9]([CH3:11])[NH:8][C:7]1=[O:12].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH:5]=[C:6]1[N:10]=[C:9]([CH3:11])[NH:8][C:7]1=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 136386015HCID 136386015, compound

Product 1

HCID 136386016HCID 136386016, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

3,5-Dihydro-5-(2′-methoxybenzylidene)-2-methylimidazol-4-one (1.28 g) was dissolved in dichloromethane (20 ml) and boron tribromide (4.5 g) was added dropwise while stirring at −40° C. Thereafter, the mixture was stirred for 2 hr under ice-cooling and the reaction mixture was poured into ice water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3,5-dihydro-5-(2′-hydroxybenzylidene)-2-methylimidazol-4-one (1 g) as red crystals. The crystals and (S)-glycidyl nosylate (1.3 g) were dissolved in dimethylformamide (20 ml) and potassium carbonate (1.38 g) was added. The mixture was heated at 50° C. for 2 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oily product (1.12 g). This oily product and 4-(naphthalen-2-yl)piperidine were dissolved in methanol (15 ml) and the mixture was refluxed under heating for 2 hr. After cooling, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (0.23 g) as an oil.

Workup

  1. stirringThereafter, the mixture was stirred for 2 hr under ice-
  2. temperaturecooling
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c1f9aeca56f4b18b8ab2347f6f7b43b
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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