Sodium hydride → 1-[6-(4-Bromophenoxy)hexyl]-3-(4-methyl-1,3-thiazol-2-yl)-2-imidazolidinone

HRID 49267Notes

Reaction equation

HRID 49267 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[S:5][CH:6]=1.[H-].[Na+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br)=[CH:18][CH:17]=1>CN(C)C=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:9]2[CH2:10][CH2:11][N:7]([C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)[C:8]2=[O:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20636586HCID 20636586, compoundHCID 224947501-Bromo-4-((6-bromohexyl)oxy)benzene

Product 1

HCID 129864891-[6-(4-Bromophenoxy)hexyl]-3-(4-methyl-1,3-thiazol-2-yl)-2-imidazolidinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-(4-methyl-1,3-thiazol-2-yl)-2-imidazolidinone (0.11 g, 0.61 mmol) dissolved in 10 mL of dimethylformamide at 0° C. was added NaH (60% dispersion in mineral oil, 36.6 mg, 0.92 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled in ice bath. 1-Bromo-4-[(6-bromohexyl)oxy] benzene (0.21 g, 0.61 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with methanol, and the solvents were removed under reduced pressure. A saturated aqueous NH4Cl solution and dichloromethane 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 10) as a yellow viscous oil (0.19 g, 74%).

Workup

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

Sources & evidence

ORD record
ord-7be298e0f9414c9584bbc1d3a7fb768e
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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