Sodium hydride → 1-[6-(1,3-Benzothiazol-2-yloxy)hexyl]-3-(3-pyridyl)-2-imidazolidinone

HRID 49261Notes

Reaction equation

HRID 49261 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:2]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1>CN(C)C=O>[S:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:9]1[CH2:10][CH2:11][N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:8]1=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 148342041-(Pyridin-3-yl)imidazolidin-2-oneHCID 20636598HCID 20636598, compound

Product 1

HCID 129864841-[6-(1,3-Benzothiazol-2-yloxy)hexyl]-3-(3-pyridyl)-2-imidazolidinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-pyridyl)-2-imidazolidinone (0.11 g, 0.65 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 31.2 mg, 0.78 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled in ice bath again. 2-[(6-Bromohexyl)oxy]-1,3-benzothiazole (0.20 g, 0.65 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvent was removed under vacuum. A saturated aqueous NH4Cl solution (5 mL) and dichloromethane (10 mL) were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 4) as a white solid (0.14 g, 88%).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturecooled in ice bath again
  3. stirringthe mixture was stirred at room temperature for additional 4 hours
  4. customThe reaction was quenched with MeOH
  5. customthe solvent was removed under vacuum
  6. additionA saturated aqueous NH4Cl solution (5 mL) and dichloromethane (10 mL) were successively added to the residue
  7. customThe dichloromethane layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. custompurified by column chromatography (ethyl acetate:MeOH=10:1)

Sources & evidence

ORD record
ord-e1fa68aed43a4cc0b57949ea7be6939a
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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