Sodium hydride → HCID 20636595, compound

HRID 49265Notes

Reaction equation

HRID 49265 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)=[CH:19][CH:18]=1>CN(C)C=O>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:10]2[CH2:11][CH2:12][N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=3)[C:9]2=[O:13])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20636580HCID 20636580, compoundHCID 22494660HCID 22494660, compound

Product 1

HCID 20636595HCID 20636595, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-chloro-4-pyridyl)-2-imidazolidinone (0.12 g, 0.63 mmol) dissolved in 10 mL dimethylformamide at 0° C. was added NaH (60% dispersion in mineral oil, 27.7 mg, 0.69 mmol). The mixture was stirred at room temperature for 30 minutes; then cooled in ice bath. 1-Bromo-4-[(7-bromoheptyl)oxy] benzene (0.22 g, 0.63 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvents were pumped off. A saturated aqueous NH4Cl solution (5 mL) and dichloromethane (10 mL) were added to the residue. The dichloromethane layer was dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 8) as a white solid (0.19 g, 64%).

Workup

  1. temperaturethen cooled in ice bath
  2. stirringthe mixture was stirred at room temperature for additional 4 hours
  3. customThe reaction was quenched with MeOH
  4. additionA saturated aqueous NH4Cl solution (5 mL) and dichloromethane (10 mL) were added to the residue
  5. dry with materialThe dichloromethane layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by column chromatography (ethyl acetate:MeOH=10:1)

Sources & evidence

ORD record
ord-0c8d8f29888942789eda31322882c208
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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