Cesium carbonate → HCID 68357024, compound

HRID 1481812Notes

Reaction equation

HRID 1481812 reaction equation
[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[NH:5][C:3]1=[O:4].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:5]2[C:6](=[O:7])[CH2:8][N:2]([CH3:1])[C:3]2=[O:4])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 692171-MethylhydantoinHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 68357024HCID 68357024, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 1-methylhydantoin (40.0 g, 351 mmol) in DMF (700 mL) at ambient temperature was added 4-methoxybenzyl chloride (49.4 g, 316 mmol) and cesium carbonate (171 g, 526 mmol). The resulting mixture was stirred for 3 days, then partitioned between H2O (2 L) and EtOAc (800 mL). The aqueous layer was extracted further with EtOAc (500 mL) and the combined organic extracts were washed with H2O (2×300 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting white precipitate was collected by vacuum filtration and washed with MTBE (200 mL) to provide the title compound. MS: m/z=235.2 (M+1).

Workup

  1. custompartitioned between H2O (2 L) and EtOAc (800 mL)
  2. extractionThe aqueous layer was extracted further with EtOAc (500 mL)
  3. washthe combined organic extracts were washed with H2O (2×300 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationThe resulting white precipitate was collected by vacuum filtration
  8. washwashed with MTBE (200 mL)

Sources & evidence

ORD record
ord-2fa53ceb890344f0a9cd2b31bb0ce6df
Source dataset
uspto-grants-2016_08
Patent number
US09409916B2

Reaction notes

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