Methyl iodide → 1-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-3-methylimidazolidin-2-one

HRID 1436408Notes

Reaction equation

HRID 1436408 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[CH2:17][CH2:16][NH:15][C:14]3=[O:18])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21]I>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[CH2:17][CH2:16][N:15]([CH3:21])[C:14]3=[O:18])[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 247384611-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]imidazolidin-2-one

Product 1

HCID 247835001-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-3-methylimidazolidin-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]imidazolidin-2-one (0.155 g, 0.480 mmol), prepared in step 2 of Example 75, was dissolved in 2.4 mL of anhydrous tetrahydrofuran and sodium hydride (60% suspension in mineral oil, 20 mg, 0.53 mmol) was added. The mixture was stirred for 20 min and then methyl iodide (0.03 mL, 0.48 mmol) was added and stirring was continued for 4 h. The reaction was quenched with saturated aqueous NH4Cl and diluted with ethyl acetate. The mixture was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (20% acetone/hexane) afforded the title compound (146 mg, 90%) as a white solid. HRMS: calcd for C13H12BrN3OS+H+, 337.99572; found (ESI, [M+H]+), 337.9954. Analytical HPLC: retention time 10.1 min, 210-370 nm the Xterra® RP18 column, 3.5%, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Workup

  1. stirringstirring
  2. waitwas continued for 4 h
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. additiondiluted with ethyl acetate
  5. washThe mixture was washed with water, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46ddb641f7c14c31b32f3448da061e75
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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